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

HRID 843671Notes

Reaction equation

HRID 843671 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-2398e90eb04b4a979ebbcad9a253196d
Source dataset
uspto-grants-2002_04
Patent number
US06380216B1

Reaction notes

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