Water → N-{[4-Phenyl-1-(3,3,3-triphenylpropyl)piperidin-4-yl]methyl}acetamide

HRID 1834150Notes

Reaction equation

HRID 1834150 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][CH2:6]1.[C:38](OC(=O)C)(=[O:40])[CH3:39].C(=O)([O-])[O-].[K+].[K+].O>C(Cl)Cl>[C:32]1([C:5]2([CH2:4][NH:3][C:38](=[O:40])[CH3:39])[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:9][CH2:10]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 20374258HCID 20374258, compound

Product 1

HCID 20374265N-{[4-Phenyl-1-(3,3,3-triphenylpropyl)piperidin-4-yl]methyl}acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1 part of 4-aminomethyl-4-phenyl-1-(3,3,3-triphenylpropyl)piperidine dihydrochloride, 1 part by volume of acetic anhydride, 1 part of potassium carbonate, 10 parts by volume of water and 10 parts by volume of methylene chloride is stirred at room temperature for about 4 hours. The organic and aqueous layers are separated, the aqueous layer washed with methylene chloride and the methylene chloride fraction combined with the organic layer. The combined organic fraction is dried over potassium carbonate, the solvent evaporated and the residual colorless amorphous solid crystallized from a mixture of n-hexane and ether to afford N-([4-phenyl-1-(3,3,3-triphenylpropyl)piperidine-4-yl]methyl)acetamide melting at about 154-167° C. This compound is represented by the following structural formula ##STR14##

Workup

  1. customThe organic and aqueous layers are separated
  2. washthe aqueous layer washed with methylene chloride
  3. dry with materialThe combined organic fraction is dried over potassium carbonate
  4. customthe solvent evaporated
  5. customthe residual colorless amorphous solid crystallized from a mixture of n-hexane and ether

Sources & evidence

ORD record
ord-579613f63ed64b6495acd5cb222b4443
Source dataset
uspto-grants-1978_01
Patent number
US04069223

Reaction notes

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