4-(3-Chloro-4-methoxy-benzoyl)-piperidine-1-carboxylic acid tert-butylester → (3-Chloro-4-methoxy-phenyl)-piperidin-4-yl-methanone

HRID 713459Notes

Reaction equation

HRID 713459 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([Cl:23])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl>[Cl:23][C:17]1[CH:16]=[C:15]([C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:24])[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

3

Reactant 1

HCID 712360784-(3-Chloro-4-methoxy-benzoyl)-piperidine-1-carboxylic acid tert-butylester

Product 1

HCID 43130928(3-Chloro-4-methoxy-phenyl)-piperidin-4-yl-methanoneYield 90.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 4-(3-chloro-4-methoxy-benzoyl)-piperidine-1-carboxylic acid tert-butylester (1.1 g, 3.1 mmol) in 20 mL of 6N HCl, the reaction mixture was stirred at ambient temperature for 18 hours, then solvent was removed by reduced pressure to yield the title product (0.75 g, 2.8 mmol). MS (ESI) m/z 254.0 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.39 min.

Workup

  1. customsolvent was removed by reduced pressure

Sources & evidence

ORD record
ord-bbc6884f33bc44b49f118a12cef36732
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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