Hydrogen Bromide → 3-(6-Methyl-6-azabicyclo(3.2.1)octan-1-yl)phenol

HRID 1580146Notes

Reaction equation

HRID 1580146 reaction equation
Br.C[O:3][C:4]1[CH:5]=[C:6]([C:10]23[CH2:18][CH:14]([N:15]([CH3:17])[CH2:16]2)[CH2:13][CH2:12][CH2:11]3)[CH:7]=[CH:8][CH:9]=1.Br>>[OH:3][C:4]1[CH:5]=[C:6]([C:10]23[CH2:18][CH:14]([N:15]([CH3:17])[CH2:16]2)[CH2:13][CH2:12][CH2:11]3)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 122866111-(3-Methoxyphenyl)-6-methyl-6-azabicyclo[3.2.1]octane--hydrogen bromide (1/1)

Product 1

HCID 417983-(6-Methyl-6-azabicyclo(3.2.1)octan-1-yl)phenolYield 88%

Procedure

A mixture of 0.4 g of 1-(3-methoxyphenyl)-6-methyl-6-azabicyclo[3,2,1]octane hydrobromide and 4 ml of aqueous 48% hydrobromic acid is refluxed for 1.5 hours. After the reaction, the mixture is concentrated under reduced pressure. Aqueous ammonia is added to the residue, and the aqueous mixture is extracted with chloroform. The chloroform extract is washed with water, dried and then evaporated to remove solvent. The residue thus obtained is recrystallized from ethylacetate. 0.245 g of 1-(3-hydroxyphenyl)-6-methyl-6-azabicyclo[3,2,1]octane is obtained. M.p. 144.5°-145.5°C.

Workup

  1. temperatureis refluxed for 1.5 hours
  2. customAfter the reaction
  3. concentrationthe mixture is concentrated under reduced pressure
  4. additionAqueous ammonia is added to the residue
  5. extractionthe aqueous mixture is extracted with chloroform
  6. extractionThe chloroform extract
  7. washis washed with water
  8. customdried
  9. customevaporated
  10. customto remove solvent
  11. customThe residue thus obtained
  12. customis recrystallized from ethylacetate

Sources & evidence

ORD record
ord-9f9b193a32934a9f8031f85811e01a59
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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