Isopropanol → HCID 19823865, compound

HRID 1650978Notes

Reaction equation

HRID 1650978 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 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-18ec38d4ece64b11b6e656bc0c84eab2
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

Loading…