1-(3-Methoxyphenyl)-6,7-dimethyl-6-azabicyclo[3.2.1]octane--hydrogen bromide (1/1) → HCID 3045735, compound

HRID 1580147Notes

Reaction equation

HRID 1580147 reaction equation
Br.C[O:3][C:4]1[CH:5]=[C:6]([C:10]23[CH2:19][CH:14]([N:15]([CH3:18])[CH:16]2[CH3:17])[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[CH2:19][CH:14]([N:15]([CH3:18])[CH:16]2[CH3:17])[CH2:13][CH2:12][CH2:11]3)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 681453441-(3-Methoxyphenyl)-6,7-dimethyl-6-azabicyclo[3.2.1]octane--hydrogen bromide (1/1)

Product 1

HCID 3045735HCID 3045735, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 3.1 g of 1-(3-methoxyphenyl)-6,7-dimethyl- 6-azabicyclo[3,2,1]octane hydrobromide and 30 ml of 48% aqueous 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. 2.1 g of 1-(3-hydroxyphenyl)-6,7-dimethyl-6-azabicyclo[3,2,1]octane is obtained.

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-a599f32fafbf42a086babc850a6eb82f
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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