4-(4-CHLORO-PHENOXY)-PIPERIDINE synthesis
- Product Name:4-(4-CHLORO-PHENOXY)-PIPERIDINE
- CAS Number:97839-99-1
- Molecular formula:C11H14ClNO
- Molecular Weight:211.69
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Yield:97839-99-1 99%
Reaction Conditions:
Stage #1: tert-butyl 4-(4-chlorophenoxy)piperidine-1-carboxylatewith trifluoroacetic acid in dichloromethane; for 5 h;
Stage #2: with sodium hydroxide in water at 5 - 10;
Steps:
64
Preparation of 4-(4-chloro-phenoxy)-piperidine To a solution of triphenyl phosphine (1.3 g, 4.96 mmol) in THF was added DIAD (753 mg, 3.72 mmol) at 0° C. and the mixture was stirred for 1 hour. A solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 2.48 mmol) and 4-chlorophenol (320 mg, 2.48 mmol) in THF was then added at 0° C. and the mixture was stirred at room temperature overnight. The mixture was then concentrated and purified through Si-gel column (2% ethyl acetate-hexane) to afford 450 mg (58%) of 4-(4-Chloro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester. To a solution of 4-(4-Chloro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (450 mg, 1.45 mmol)) in DCM was added trifluoroacetic acid (1.1 ml, 14.5 mmol) and the solution was stirred for about 5 hours. The reaction mass was then concentrated and washed with dry ether. The TFA salt was diluted with a minimum volume of water and neutralized with aq. NaOH solution at 5-10° C. Extraction of the neutralized solution followed by concentration afforded 300 mg (99%) of 4-(4-Chloro-phenoxy)-piperidine. LC/MS [M+H]+: 212.3
References:
US2010/168080,2010,A1 Location in patent:Page/Page column 57-58
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