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

HRID 719299Notes

Reaction equation

HRID 719299 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-7ada5aa870944544acb8787642ce2a61
Source dataset
uspto-grants-2006_11
Patent number
US07132433B2

Reaction notes

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