ChemicalBook CAS DataBase List 1-BENZYL 4-ETHYL PIPERIDINE-1,4-DICARBOXYLATE

1-BENZYL 4-ETHYL PIPERIDINE-1,4-DICARBOXYLATE synthesis

3synthesis methods

Product Name:1-BENZYL 4-ETHYL PIPERIDINE-1,4-DICARBOXYLATE
CAS Number:160809-38-1
Molecular formula:C16H21NO4
Molecular Weight:291.34

1126-09-6 Synthesis

1126-09-6
485 suppliers
$15.40/25g

501-53-1
396 suppliers
$10.00/1g

1-BENZYL 4-ETHYL PIPERIDINE-1,4-DICARBOXYLATE

160809-38-1
93 suppliers
$38.00/1g

Yield: 94%

Reaction Conditions:

with sodium carbonate in dichloromethane at 0 - 20; for 60 h;

Steps:

1 DESCRIPTION 1; Piperidine-1, 4-dicarboxylic acid 1-benzyl ester 4-ethyl ester
A solution of benzyl chloroformate (95g, 0. 56mol) in dichloromethane (200ml) was added dropwise to an ice-bath-cooled, stirred mixture of ethyl isonipecotate (87G, 0. 55MOL), sodium carbonate (60g, 0. 57mol) and dichloromethane (200ml) over 70 minutes. The mixture was stirred at ambient temperature for 2.5 days and filtered though a pad of Celte. The filtrate was concentrated in vacuo. The residue was partitioned between 2M aqueous hydrochloric acid and diethyl ether. Organic layer was separated, dried (MGS04), filtered and concentrated. The residue was chromatographed on silica gel (ethyl ACETATE/ISO-HEXANE) to give the title product (152g, 94%). lE NMR (360 MHz, CDCl3) : 5 7. 4 1-7. 27 (5H, M), 5.12 (2EI, s), 4.22-3. 99 (2H, M), 4. 14 (2H, Q, J7. 4HZ), 2.93 (2H, br T, J 11. 6HZ), 2.45 (2H, m), 1.97-1. 81 (2H, M), 1.74-1. 56 (2EI, m), 1. 25 (3H, T, J7. 4Hz).

References:

MERCK SHARP & DOHME LIMITED WO2004/78750, 2004, A1 Location in patent:Page 64