Isopropanol → HCID 19823865, compound

HRID 728301Notes

Reaction equation

HRID 728301 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:21]([CH3:23])[CH3:22])[CH2:13][CH2:14][CH2:15][O:16][CH2:17][C:18](=[O:20])[CH3:19])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].CC(O)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:12]([N:21]([CH3:23])[CH3:22])[CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH:18]([OH:20])[CH3:19])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 19823659HCID 19823659, compound

Product 1

HCID 19823865HCID 19823865, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-{4-[1-(4-chlorophenyl)cyclobutyl]-4-dimethylaminobutoxy}propan-2-one (1.4 g prepared as described in Example 214) sodium borohydride (1.5 g) and propan-2-ol (30 ml) was heated under reflux for 4.25 hours. The mixture was cooled and poured into water. The aqueous mixture was extracted with ether. The extract was dried and evaporated to give a residue which was heated at 90°/20 mm to leave 1-{4-[1-(4-chlorophenyl)cyclobutyl]-4-dimethylaminobutoxy}propan-2-ol as an oil the boiling point of which was not determined.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4.25 hours
  3. temperatureThe mixture was cooled
  4. extractionThe aqueous mixture was extracted with ether
  5. customThe extract was dried
  6. customevaporated
  7. customto give a residue which
  8. temperaturewas heated at 90°/20 mm

Sources & evidence

ORD record
ord-eec044aef3934b1dad38088699b860c2
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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