Hydrochloric Acid → HCID 19823812, compound

HRID 728266Notes

Reaction equation

HRID 728266 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:16]([CH3:18])[CH3:17])[C:13](=[O:15])[CH3:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].S(=O)(=O)(O)O.Cl>C(O)C.CC(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:12]([N:16]([CH3:17])[CH3:18])[CH:13]([OH:15])[CH3:14])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 19823745HCID 19823745, compound

Product 1

HCID 19823812HCID 19823812, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3776IsopropanolSolvent

Procedure

A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminopropan-2-one (1.9 g prepared as described in Example 47) in ethanol (10 ml) was added dropwise to a suspension of sodium borohydride (0.4 g) in ethanol (20 ml) and the mixture was stirred for 4 hours at ambient temperature. 5N Sulphuric acid (10 ml) was added and then the acidified mixture was basified. The resulting mixture was extracted with ether and the ether extracts were washed with water and dried. Removal of the solvent gave 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 after the removal of the solvents was dried by azeotropic distillation with propan-2-ol to give 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminopropan-2-ol hydrochloride (m.p. 255° C.).

Workup

  1. extractionThe resulting mixture was extracted with ether
  2. washthe ether extracts were washed with water
  3. customdried
  4. customRemoval of the solvent
  5. customgave an oil which
  6. customThe residue after the removal of the solvents
  7. dry with materialwas dried by azeotropic distillation with propan-2-ol

Sources & evidence

ORD record
ord-e3904951298b43fbae4b4e3b4796d1d7
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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