Hydrogen Bromide → 7-Hydroxy-3-piperidino-2,2-dimethylbenzofuran

HRID 3774

Reaction equation

HRID 3774 reaction equation
C[O:2][C:3]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH:8]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[C:11]2[O:10][C:9]([CH3:12])([CH3:13])[CH:8]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 141266497-Methoxy-3-piperidino-2,2-dimethylbenzofuran

Product 1

HCID 141266507-Hydroxy-3-piperidino-2,2-dimethylbenzofuran

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-Methoxy-3-piperidino-2,2-dimethylbenzofuran (65.1 g) is added to a stirred mixture of glacial acetic acid (340 ml) and 48% HBr (340 ml) and the solution refluxed for 3 hours. The reaction mixture is poured into crushed ice/H2O and brought to a pH=8-10. The alkaline reaction mixture is extracted with methylene chloride and the organic phase washed with water, dried, filtered and evaporated in vacuo. The residue is chromatographed on silica gel eluting with ethyl acetate/hexane (1:3) affording the desired product as a liquid.

Workup

  1. temperaturethe solution refluxed for 3 hours
  2. additionThe reaction mixture is poured
  3. customThe alkaline reaction mixture
  4. extractionis extracted with methylene chloride
  5. washthe organic phase washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue is chromatographed on silica gel eluting with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-62c89f061fa24da181f2e8c2e39d52b5
Source dataset
uspto-grants-1988_02
Patent number
US04722925

Linked notes

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