Diethyl Ether → 4-(2,3-Dimethoxyphenyl)-4-piperidinylmethanone trifluoroacetate

HRID 1166181Notes

Reaction equation

HRID 1166181 reaction equation
CC(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])C=2OC)[CH2:10][CH2:9]1)=O)(C)C.[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].C[CH2:34][O:35]CC>>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[CH3:22][O:21][C:17]1[C:18]([O:35][CH3:34])=[CH:19][CH:20]=[CH:15][C:14]=1[C:11]1([CH:28]=[O:30])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 46780868N-Boc-(2,3-dimethoxyphenyl)-4-piperidinylmethanone

Product 1

HCID 218981094-(2,3-Dimethoxyphenyl)-4-piperidinylmethanone trifluoroacetate

Procedure

4-(2,3-Dimethoxybenzoyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (7.75 g, 22.2 mmol) was dissolved in trifluoroacetic acid (50 mL, 650 mmol) and stirred for 45 minutes. The entire solution was poured into ether (900 mL) and allowed to stand overnight. Filtration yielded 4-(2,3-dimethoxyphenyl)-4-piperidinylmethanone trifluoroacetate as fine white needles, m.p. 123° C. Anal. Calcd. for C14H19NO3.CF3CO2H: C, 52.89; H, 5.55; N, 3.86. Found: C, 52.77; H, 5.62; N, 3.82.

Workup

  1. waitto stand overnight
  2. filtrationFiltration

Sources & evidence

ORD record
ord-5945f26b31264b049970230467afde76
Source dataset
uspto-grants-2003_09
Patent number
US06613779B2

Reaction notes

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