Acetic Anhydride → HCID 20370896, compound

HRID 616205Notes

Reaction equation

HRID 616205 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]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([CH2:17][OH:18])[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:2]1([C:8]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)([CH2:17][O:18][C:37](=[O:39])[CH3:38])[CH2:13][CH2:12]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20370855[4-Phenyl-1-(3,3,3-triphenylpropyl)piperidin-4-yl]methanol--hydrogen chloride (1/1)

Product 1

HCID 20370896HCID 20370896, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.0 part of 1-(3,3,3-triphenylpropyl)-4-phenyl-4-piperidinemethanol 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-phenyl-4-acetoxymethylpiperidine hydrochloride melting at about 211°-213° C 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-phenyl-4-propionyloxymethylpiperidine 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-14de6428217c468dbef21b765b53181d
Source dataset
uspto-grants-1978_02
Patent number
US04072686

Reaction notes

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