Acetic Anhydride → N-{4-[(4-benzhydryl-1-piperidinyl)methyl]phenyl}acetamide

HRID 258823Notes

Reaction equation

HRID 258823 reaction equation
[C:1]1([CH:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>C(O)(=O)C>[C:28]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:11]2[CH2:10][CH2:9][CH:8]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:13][CH2:12]2)=[CH:20][CH:19]=1)(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 202258204-{[4-(Diphenylmethyl)-1-piperidinyl]methyl}benzenamine

Product 1

HCID 21424837N-{4-[(4-benzhydryl-1-piperidinyl)methyl]phenyl}acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 8 parts of 4-{[4-(diphenylmethyl)-1-piperidinyl]methyl}benzenamine in 50 parts of acetic acid is added 5 parts of acetic anhydride. The resultant mixture is heated to the boiling point under reflux and maintained thereat for 10 minutes, then stripped of solvents by vacuum distillation. The residue is combined with 10 volumes of water. The resultant mixture is made alkaline with concentrated ammonium hydroxide. The mixture thus obtained is extracted with dichloromethane. The dichloromethane extract is dried over anhydrous potassium carbonate and then stripped of solvent by vacuum distillation. The residue, recrystallized from benzene, affords N-acetyl-4-{[4-(diphenylmethyl)-1-piperidinyl]methyl}benzenamine melting at approximately 182°-183°. The product has the formula ##STR5##

Workup

  1. temperatureunder reflux
  2. temperaturemaintained
  3. distillationstripped of solvents by vacuum distillation
  4. customThe mixture thus obtained
  5. extractionis extracted with dichloromethane
  6. extractionThe dichloromethane extract
  7. dry with materialis dried over anhydrous potassium carbonate
  8. distillationstripped of solvent by vacuum distillation
  9. customThe residue, recrystallized from benzene

Sources & evidence

ORD record
ord-d664fea9c1b846caac6ca05eb08f8072
Source dataset
uspto-grants-1977_07
Patent number
US04035372

Reaction notes

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