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[ CAS No. 15486-96-1 ] {[proInfo.proName]}

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Chemical Structure| 15486-96-1
Chemical Structure| 15486-96-1
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Product Details of [ 15486-96-1 ]

CAS No. :15486-96-1 MDL No. :MFCD00000746
Formula : C3H4BrClO Boiling Point : No data available
Linear Structure Formula :ClC(O)CH2CH2Br InChI Key :IHBVNSPHKMCPST-UHFFFAOYSA-N
M.W : 171.42 Pubchem ID :84944
Synonyms :

Safety of [ 15486-96-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:1760
Hazard Statements:H314-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 15486-96-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 15486-96-1 ]

[ 15486-96-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 36725-28-7 ]
  • [ 15486-96-1 ]
  • [ 101328-86-3 ]
  • 2
  • [ 525-03-1 ]
  • [ 15486-96-1 ]
  • [ 879216-96-3 ]
  • 3
  • [ 15486-96-1 ]
  • [ 3433-74-7 ]
  • 3-bromo-1-(11H-10-oxa-5-aza-5H-dibenzo[a,d]cyclohepten-5-yl)propane [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.8 g (13%) With sodium hydroxide; sodium borohydrid; trifluoroborane diethyl ether; In tetrahydrofuran; water; ethyl acetate; toluene; Example 12 (R)-1-(3-(11H-10-Oxa-5-aza-5H-dibenzo[a,d]cyclohepten-5-yl)-1-propyl)-3-piperidinecarboxylic acid hydrochloride In a 500 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel <strong>[3433-74-7]5,11-dihydro-10-oxa-5-azadibenzo[a,d]cycloheptene</strong> (4.0 g, 0.02 mol, prepared in a similar way as described in J. Med. Chem., 7, (1964), 609) was dissolved in dry toluene (50 ml) and 3-bromopropionyl chloride (4.2 g, 0.024 mol) was slowly added. The reaction mixture was heated to 95 C. for 30 minutes and then allowed to cool to room temperature. Under stirring 0.2N NaOH (10 ml) was added. More toluene was added (50 ml) and the phases were separated. The organic phase was washed with 0.2N NaOH (3*20 ml) until pH>10, and then with water (3*20 ml) and brine (20 ml). After drying (MgSO4), the organic phase was evaporated in vacuo affording an oil. The product was obtained in quantitative yield and used for further reactions without purification. The above amide (3.5 g, 0.01 mol) was dissolved in dry THF (20 ml) under a nitrogen atmosphere and cooled to 5 C. Sodium borohydride (0.31 g, 0.008 mol) was added followed by slow dropwise addition of boron trifluoride etherate (2.0 ml, 0.016 mol). The reaction mixture was left stirring overnight. Further amounts of sodium borohydride (1.2 g. 0.032 mol) and boron trifluoride etherate (5 ml, 0.040 mol) were supplied, and stirring was continued overnight. Water was added to dissolve precipitated salt, followed by ethyl acetate (100 ml). The phases were separated, and the aqueous phase was extracted with ethyl acetate (2*100 ml). The combined organic extracts were washed with water (4*100 ml) and brine (100 ml). After drying (MgSO4) the solvent was removed by evaporation in vacuo and the crude product was purified by column chromatography on silica gel (200 g) with dichloromethane as eluent. This afforded 0.8 g (13%) of the product, 3-bromo-1-(11H-10-oxa-5-aza-5H-dibenzo[a,d]cyclohepten-5-yl)propane. Rf: 0.62 (SiO2; dichloromethane).
0.8 g (13%) With sodium hydroxide; sodium borohydrid; trifluoroborane diethyl ether; In tetrahydrofuran; water; ethyl acetate; toluene; Example 12 (R)-1-(3-(11H -10-Oxa-5-aza-5H-dibenzo[a,d]cyclohepten-5-yl)-1-propyl)-3-piperidinecarboxylic acid hydrochloride In a 500 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel <strong>[3433-74-7]5,11-dihydro-10-oxa-5-azadibenzo[a,d]cycloheptene</strong> (4.0 g, 0.02 mol, prepared in a similar way as described in J. Med. Chem., 7, (1964), 609) was dissolved in dry toluene (50 ml) and 3-bromopropionyl chloride (4.2 g, 0.024 mol) was slowly added. The reaction mixture was heated to 95 C. for 30 minutes and then allowed to cool to room temperature. Under stirring 0.2N NaOH (10 ml) was added. More toluene was added (50 ml) and the phases were separated. The organic phase was washed with 0.2N NaOH (3*20 mi) until pH >10, and then with water (3*20 ml) and brine (20 ml). After drying (MgSO4), the organic phase was evaporated in vacuo affording an oil. The product was obtained in quantitative yield and used for further reactions without purification. The above amide (3.5 g, 0.01 mol) was dissolved in dry THF (20 ml) under a nitrogen atmosphere and cooled to 5 C. Sodium borohydride (0.31 g, 0.008 mol) was added followed by slow dropwise addition of boron trifluoride etherate (2.0 ml, 0.016 mol). The reaction mixture was left stirring overnight. Further amounts of sodium borohydride (1.2 g. 0.032 mol) and boron trifluoride etherate (5 ml, 0.040 mol) were supplied, and stirring was continued overnight. Water was added to dissolve precipitated salt, followed by ethyl acetate (100 ml). The phases were separated, and the aqueous phase was extracted with ethyl acetate (2*100 ml). The combined organic extracts were washed with water (4*100 ml) and brine (100 ml). After drying (MgSO4) the solvent was removed by evaporation in vacuo and the crude product was purified by column chromatography on silica gel (200 g) with dichloromethane as eluent. This afforded 0.8 g (13%) of the product, 3-bromo-1-(11H-10-oxa-5-aza-5H-dibenzo[a,d]cyclohepten-5-yl)propane. Rf: 0.62 (SiO2; dichloromethane).
  • 4
  • [ 5369-19-7 ]
  • [ 15486-96-1 ]
  • [ 1281991-38-5 ]
  • 5
  • [ 580-15-4 ]
  • [ 15486-96-1 ]
  • 3-bromo-N-(6-quinolyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With dmap; In tetrahydrofuran; at 0 - 20℃; General procedure: A solution of the appropriate amine (1 equiv) and 4-(dimethylamino)pyridine (DMAP) (0.47 equiv) in dry THF was added dropwise to a solution of 3-bromopropionyl chloride (1.5equiv) in THF (10mL) cooled at 0C. The reaction mixture was kept under vigorous stirring at rt for 4h and then was quenched with H2O and extracted with CHCl3. The organic phase was washed with a saturated aqueous solution of NaHCO3 and brine, and dried over anhydrous Na2SO4. After the solvent was removed in vacuo, the residue was purified by flash chromatography using a silica gel column with a cyclohexane/AcOEt (7/3) solvent system to give the compounds (1-7) as solids.
  • 6
  • [ 15486-96-1 ]
  • [ 302348-51-2 ]
  • C16H22BBrO4 [ No CAS ]
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