Water → HCID 178481190, compound

HRID 1704628Notes

Reaction equation

HRID 1704628 reaction equation
[C@@H:1]12[N:8]([CH3:9])[C@@H:5]([CH2:6][CH2:7]1)[CH2:4][C@H:3]([OH:10])[CH2:2]2.[Cl:11][C:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13].O>C1C=CC=CC=1>[ClH:11].[O:14]([C:12]([O:10][C@H:3]1[CH2:2][C@H:1]2[N:8]([CH3:9])[C@H:5]([CH2:6][CH2:7]2)[CH2:4]1)=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 15891Phenyl chloroformateHCID 178481185HCID 178481185, compound

Product 1

HCID 178481190HCID 178481190, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 14.1 g (0.1 moles) of tropane-3β-ol (pseudotropine) in 60 ml of absolute benzene is added dropwise to a stirred mixture of 31.3 g (0.2 moles) of phenyl chloroformate and 100 ml of absolute benzene. During addition the mixture is cooled with water. Thereafter the mixture is stirred for 6 hours. The separated crystalline substance is filtered off, washed with benzene and dried. 19.00 g (63.8%) of 3β-phenoxycarbonyloxy-tropane hydrochloride are obtained.

Workup

  1. additionDuring addition the mixture
  2. filtrationThe separated crystalline substance is filtered off
  3. washwashed with benzene
  4. customdried

Sources & evidence

ORD record
ord-10bf7fca4a194fe49e064dd2e717d92b
Source dataset
uspto-grants-1978_11
Patent number
US04127576

Reaction notes

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