ChemicalBook CAS DataBase List N-BOC-4-(4'-CHLORO) BENZYL-4-PIPERIDINE CARBOXYLIC ACID

N-BOC-4-(4'-CHLORO) BENZYL-4-PIPERIDINE CARBOXYLIC ACID synthesis

6synthesis methods

Product Name:N-BOC-4-(4'-CHLORO) BENZYL-4-PIPERIDINE CARBOXYLIC ACID
CAS Number:170284-71-6
Molecular formula:C18H24ClNO4
Molecular Weight:353.84

1-BOC-4-[(4-CHLOROPHENYL)METHYL]-4-PIPERIDINECARBOXYLIC ACID METHYL ESTER

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N-BOC-4-(4'-CHLORO) BENZYL-4-PIPERIDINE CARBOXYLIC ACID

170284-71-6
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Yield:170284-71-6 100%

Reaction Conditions:

Stage #1: 4-(4-chlorobenzyl)piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl esterwith methanol;lithium hydroxide;water in 1,4-dioxane at 50; for 48 h;
Stage #2: with hydrogenchloride in 1,4-dioxane;methanol;water; pH=6;

Steps:

38.38B

38B. 4-(4-Chlorobenzv?piperidine-l,4-dicarboxylic acid mono-fert-butyl ester; To a solution of 4-(4-chlorobenzyl)piperidine-l,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (1.515 g, 4.117 mmol) in dioxane (20 ml), methanol (10 ml) and water (10 ml) at room temperature was added lithium hydroxide monohydrate (3.455 g, 82.341 mmol). After stirring at 50 ⁰C for 2 days the solution was acidified to pH 6 with 2M HCl and the resulting white precipitate was extracted with diethyl ether (2 x 100 ml). The organic phases were combined, dried over sodium sulphate and concentrated to dryness, to give the acid as a white solid (1.460 g, 100%). LC/MS (LCTl): R_t 7.62 [M+Na⁺] 376.

References:

WO2006/51290,2006,A2 Location in patent:Page/Page column 142