Methanol → HCID 20225041, compound

HRID 1249163Notes

Reaction equation

HRID 1249163 reaction equation
[C:1]([C:4]1([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CO.[BH4-].[Na+]>O>[ClH:14].[CH2:16]([NH:23][CH:1]([C:4]1([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:2])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7504BenzylamineHCID 4311764Sodium borohydrideHCID 130831391-Acetyl-1-(3,4-dichlorophenyl)cyclobutane

Product 1

HCID 20225041HCID 20225041, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Acetyl-1-(3,4-dichlorophenyl)cyclobutane (4.86 g) and benzylamine (2.2 ml) were stirred at a temperature of 140° to 150° C. under nitrogen for 1 hour 30 minutes. Methanol (50 ml) was added to the cooled reaction mixture and sodium borohydride (0.8 g) was added over a period of ten minutes. The mixture was stirred at ambient temperature for two hours and then the volume of the reaction mixture was reduced by a half and the mixture poured into water (300 ml). The aqueous mixture was extracted with ether and the ether extract dried and the ether removed by evaporation. The residue was distilled (b.p. 182°-186° at 0.5 mm Hg) and the distillate treated with hydrogen chloride in ether to give N-benzyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine hydrochloride (m.p. 227°-228° C.).

Workup

  1. additionwas added over a period of ten minutes
  2. extractionThe aqueous mixture was extracted with ether
  3. extractionthe ether extract
  4. customdried
  5. customthe ether removed by evaporation
  6. distillationThe residue was distilled (b.p. 182°-186° at 0.5 mm Hg)
  7. additionthe distillate treated with hydrogen chloride in ether

Sources & evidence

ORD record
ord-11f70b7e82ff499996548901ddfce7cf
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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