Water → HCID 15480808, compound

HRID 1058611Notes

Reaction equation

HRID 1058611 reaction equation
[C:1]1([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:36](Br)[CH3:37].O>CN(C)C=O.C(OCC)(=O)C>[C:24]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([O:17][CH2:36][CH3:37])=[O:16])[CH2:10][CH2:9]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 15480813HCID 15480813, compound

Product 1

HCID 15480808HCID 15480808, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 23.6 g of N-triphenylmethyl-4-piperidineacetic acid, 16.9 g of potassium carbonate and 5.0 ml of ethyl bromide in 230 ml of dried N,N-dimethylformamide was stirred at 90° C. for 5 hours. After cooling, the reaction mixture was added with water and ethyl acetate, and the precipitated crystals were collected by filtration and washed with water to give 20.6 g of colorless crystals. Recrystallization from a mixture of methanol and tetrahydrofuran gave colorless crystals having the melting point of from 165 to 166° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-7124bda090c1425cbff146187a9e9631
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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