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CAS No. : | 6940-76-7 | MDL No. : | MFCD00001096 |
Formula : | C3H6ClI | Boiling Point : | - |
Linear Structure Formula : | I(CH2)3Cl | InChI Key : | SFOYQZYQTQDRIY-UHFFFAOYSA-N |
M.W : | 204.44 | Pubchem ID : | 81363 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | A solution of morpholine (2 mL, 23.0 mmol) in /V,A/-dimethylformamide (15 mL) was treated with potassium carbonate (4.75g, 34.4 mmol) and1-chloro-3-iodopropane (3.7 mL, 34.4 mmol). After 16h, the reaction mixture was partitioned between EtOAc and H20. The aqueous layer was washed with EtOAc(15x). The combined organic layers were dried (Na2S04) and concentrated. 1H NMR indicated a very large amount of DMF still remaining, so the product was taken up in EtOAc and washed with H20. The organic layer was washed with brine, dried (Na2S04) and concentrated. The resulting pale yellow oil was taken up in Et20 and treated with 4N HCI in dioxane to precipitate the product, affording 1.45g (32%) of the hydrochloride salt of 4-(3-chloropropyl)morpholine as a white solid. 1H NMR (D20): 8 3.94 (br m, 2H), 3.70 (brm, 2H), 3.53 (m, 2H), 3.15 (brm, 2H), 3.19 (m, 2H), 3.10 (brm, 2H), 2.08 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Synthesis of ethyl 5-chloro-2-(tetrahydropyran-4-yl)-valerate 672 mg of the title compound was obtained from ethyl (tetrahydropyran-4-yl)acetate (CAS No. 103260-44-2, 650 mg) and 1-chloro-3-iodopropane (0.61 ml) according to the method in Example 113. The property value of the compound is as follows. ESI-MS; m/z 249 [M++H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With triethylamine; In tetrahydrofuran; | Embodiment 6 Preparation of 1-ethoxycarbonyl-4-(3-chloropropyl)-3-pyrrolidone <strong>[1027-35-6]1-benzyl-4-ethoxycarbonyl-3-pyrrolidone</strong> (2.5 g, 10.1 mmol) is dissolved in 25 ml tetrahydrofuran and then cooled by ice water bath, triethylamine (2 g, 20.2 mmol) is added and stirring is performed for 30 minutes, 1-chloro-3-iodopropane (4.12 g, 20.2 mmol) is dripped, this dripping is finished 30 minutes later, afterwards, the temperature is raised to room temperature for the purpose of continuous reaction for 18 hours. Extraction is carried out by methylene dichloride (10 ml*3 times) at the end of reaction, organic phase is combined and dried by anhydrous sodium sulfate, and the solvent is dried by concentration under reduced pressure to obtain oily product, which is then purified by column chromatography to obtain oily product (6-1) (2.12 g, 6.57 mmol, yield 65percent). 1H NMR (500 MHz, CDCl3) delta7.34-7.27 (m, 5H), 4.17 (q, J=7.1 Hz, 2H), 3.71 (s, 2H), 3.48-3.51 (m, 2H), 3.40 (d, J=9.6 Hz, 1H), 3.19 (d, J=17.2 Hz, 1H), 2.99 (d, J=17.2 Hz, 1H), 2.73 (d, J=9.6 Hz, 1H), 2.04-2.02 (m, 1H), 1.92-1.89 (m, 2H), 1.71-1.69 (m, 1H), 1.24 (t, J=7.1 Hz, 3H). MS-ESI: m/z: 324 (M++1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | <strong>[1027-35-6]1-benzyl-4-ethoxycarbonyl-3-pyrrolidone</strong> (2.5g, 10.1mmol) is dissolved in 25ml tetrahydrofuran and then cooled by ice water bath, triethylamine (2g, 20.2mmol) is added and stirring is performed for 30 minutes, 1-chloro-3-iodopropane (4.12g, 20.2mmol) is dripped, this dripping is finished 30 minutes later, afterwards, the temperature is raised to room temperature for the purpose of continuous reaction for 18 hours. Extraction is carried out by methylene dichloride (10ml × 3 times) at the end of reaction, organic phase is combined and dried by anhydrous sodium sulfate, and the solvent is dried by concentration under reduced pressure to obtain oily product, which is then purified by column chromatography to obtain oily product (6-1) (2.12g, 6.57mmol, yield 65percent). 1H NMR (500 MHz, CDCl3) delta7.34-7.27 (m, 5H), 4,17 (q, J = 7.1Hz, 2H), 3.71(s, 2H), 3.48-3.51(m, 2H), 3.40 (d, J = 9.6Hz ,1H), 3.19 (d, J = 17.2Hz,1H), 2.99 (d, J =17.2Hz,1H), 2.73 (d, J = 9.6Hz, 1H),2.04-2.02(m, 1H),1.92-1.89(m,2H),1.71-1.69(m, 1H),1.24(t, J = 7.1Hz, 3H). MS-ESI: m/z:324(M++1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.27 g | With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 5h;Inert atmosphere; | To a solution of 2,6-dichloro- 4-iodo-phenol (1) (1.0 g, 3.46 mmol) in DMF (20 mL) was added l-chloro-3-iodo-propane (2) (708 mg, 3.46 mmol) and CS2CO3 (2.26 g, 6.92 mmol) under N2 atmosphere at 20 C. The reaction was stirred at 60 C for 5 hours. TLC showed the reaction was completed. The solution was poured into H2O (20 mL), extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine (50 mL x 3), dried over NaiSOr. filtered and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography to give 1,3- dichloro-2-(3-chloropropoxy)-5-iodobenzene (80.0 %, 1.27 g, yield: 80.3 %) as brown oil. NMR(400MHz, CHCb-d) d 7.63 (s, 2H), 4.15 (t, .7=5.7 Hz, 2H), 3.85 (t, 7=6.4 Hz, 2H), 2.28 (t..7=6. 1 Hz. 2H). |