Acetic Anhydride → HCID 22768454, compound

HRID 1764465Notes

Reaction equation

HRID 1764465 reaction equation
[ClH:1].[C:2]1([C:8]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([OH:24])([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>N1C=CC=CC=1>[ClH:1].[C:31]1([C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([O:24][C:37](=[O:39])[CH3:38])([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:13][CH2:12]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 69868284HCID 69868284, compound

Product 1

HCID 22768454HCID 22768454, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.0 part of 1-(3,3,3-triphenylpropyl)-4-hydroxy-4-benzyl piperidine hydrochloride, 10 parts by volume of pyridine and 3.0 parts by volume of acetic anhydride is allowed to stand for 24 hours. Volatile material is removed under reduced pressure and the resulting residue is partitioned between dilute sodium hydroxide and ether. The ether layer is separated, washed with water, dried over sodium sulfate and then treated with an excess of a solution of hydrogen chloride in 2-propanol. The solid which forms is separated by filtration and then washed successively with ether, water, and ether, and then air-dried to give 1-(3,3,3-triphenylpropyl)-4-acetoxy-4-benzylpiperidine hydrochloride and having the following structural formula ##STR19## Replacement of acetic anhydride with 3.0 parts of propionic acid anhydride provides 1-(3,3,3-triphenylpropyl)-4-propionyloxy-4-benzylpiperidine hydrochloride.

Workup

  1. customVolatile material is removed under reduced pressure
  2. customthe resulting residue is partitioned between dilute sodium hydroxide and ether
  3. customThe ether layer is separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. additiontreated with an excess of a solution of hydrogen chloride in 2-propanol
  7. customThe solid which forms is separated by filtration
  8. washwashed successively with ether, water, and ether
  9. customair-dried

Sources & evidence

ORD record
ord-50394441364e4c76b646ad001014998c
Source dataset
uspto-grants-1978_09
Patent number
US04116963

Reaction notes

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