Hydrogen Bromide → 3-(6-Azabicyclo[3.2.1]octan-1-yl)phenol--hydrogen bromide (1/1)

HRID 1580142Notes

Reaction equation

HRID 1580142 reaction equation
C(O)(=O)C(O)=O.C[O:8][C:9]1[CH:10]=[C:11]([C:15]23[CH2:22][CH:19]([NH:20][CH2:21]2)[CH2:18][CH2:17][CH2:16]3)[CH:12]=[CH:13][CH:14]=1.[BrH:23]>>[BrH:23].[OH:8][C:9]1[CH:10]=[C:11]([C:15]23[CH2:22][CH:19]([NH:20][CH2:21]2)[CH2:18][CH2:17][CH2:16]3)[CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 3045728Oxalic acid--1-(3-methoxyphenyl)-6-azabicyclo[3.2.1]octane (1/1)

Product 1

HCID 30457773-(6-Azabicyclo[3.2.1]octan-1-yl)phenol--hydrogen bromide (1/1)

Procedure

A mixture of 9 g of 1-(3-methoxyphenyl)-6-azabicyclo[ 3,2,1]octane oxalate and 90 ml of aqueous 48% hydrobromic acid is refluxed for 1.5 hours. After the reaction, the mixture is concentrated under reduced pressure. The residue thus obtained is recrystallized from a mixture of ethanol and ether. 7.7 g of 1-(3-hydroxyphenyl)-6-azabicyclo[3,2,1]octane hydrobromide are obtained. M.p. 239° - 242°C.

Workup

  1. temperatureis refluxed for 1.5 hours
  2. customAfter the reaction
  3. concentrationthe mixture is concentrated under reduced pressure
  4. customThe residue thus obtained
  5. customis recrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-10a0f66228cb4a6dadc2720ce7f8e9d0
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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