Hydrochloric Acid → HCID 23052561, compound

HRID 728268Notes

Reaction equation

HRID 728268 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:18]([CH3:20])[CH3:19])[C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].S(=O)(=O)(O)O.[OH-].[Na+].Cl>CC(O)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:12]([N:18]([CH3:20])[CH3:19])[CH:13]([OH:17])[CH:14]([CH3:15])[CH3:16])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride2×HCID 19823620HCID 19823620, compound

Product 1

HCID 23052561HCID 23052561, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylamino-3-methylbutan-2-one in the form in the from of its free base (4 g prepared as described in Example 49) in industrial methylated spirit (18 ml) was added dropwise to a stirred suspension of sodium borohydride (0.7 g) in industrial methylated spirit (40 ml) and the mixture was stirred for 16 hours. Sodium borohydride (0.7 g) was added and the mixture heated under reflux for 3 hours. After cooling the mixture was poured into water and acidified with concentrated sulphuric acid. 5N Sodium hydroxide solution was added with cooling and the basic aqueous liquors were extracted with ether. The extracts were washed with water and dried and the solvent was removed by evaporation to leave an oil which was converted into a hydrochloride salt by treatment with a mixture of excess concentrated hydrochloric acid and propan-2-ol. The residue was dried by azeotropic distillation with propan-2-ol to give 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylamino-3-methylbutan-2 -ol hydrochloride (m.p. 229°-231° C.).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling the mixture
  4. temperaturewith cooling
  5. extractionthe basic aqueous liquors were extracted with ether
  6. washThe extracts were washed with water
  7. customdried
  8. customthe solvent was removed by evaporation
  9. customto leave an oil which
  10. dry with materialThe residue was dried by azeotropic distillation with propan-2-ol

Sources & evidence

ORD record
ord-ae2c01c629e745a3b83ab96e764cf15d
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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