Hydrochloric Acid → HCID 19823662, compound

HRID 728267Notes

Reaction equation

HRID 728267 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:13]([N:18]([CH3:20])[CH3:19])[C:14](=[O:17])[CH2:15][CH3:16])[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].S(=O)(=O)(O)O.Cl>CC(O)C.O>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH:13]([N:18]([CH3:20])[CH3:19])[CH:14]([OH:17])[CH2:15][CH3:16])[CH2:10][CH2:11][CH2:12]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 19823872HCID 19823872, compound

Product 1

HCID 19823662HCID 19823662, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminobutan-2-one (3 g prepared as described in Example 48) in industrial methylated spirit (15 ml) was added dropwise to a stirred suspension of sodium borohydride (0.6 g) in industrial methylated spirit (30 ml) and the mixture was stirred at ambient temperature for two hours. The reaction mixture was heated under reflux for two hours, cooled and poured into water. Concentrated sulphuric acid was added and the acidified mixture was cooled in an ice bath and basified. The aqueous mixture was extracted with ether and the extract dried. Removal of the solvent by evaporation gave an oil which was treated with a mixture of excess concentrated hydrochloric acid and propan-2-ol and then the solvents were removed by evaporation. The residue was dried by azeotropic distillation with propan-2-ol to give a solid which was recrystallised from propan-2-ol to give 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminobutan-2-ol hydrochloride (m.p. 224°-227° C.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for two hours
  3. temperaturecooled
  4. temperaturethe acidified mixture was cooled in an ice bath
  5. extractionThe aqueous mixture was extracted with ether
  6. customthe extract dried
  7. customRemoval of the solvent
  8. customby evaporation
  9. customgave an oil which
  10. customthe solvents were removed by evaporation
  11. dry with materialThe residue was dried by azeotropic distillation with propan-2-ol
  12. customto give a solid which
  13. customwas recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-d5e734505d314fbb9e24a7a3d9069a8e
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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