Methanol → 1-[1-(3,4-Dichlorophenyl)cyclobutyl]ethylamine

HRID 1248141Notes

Reaction equation

HRID 1248141 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].C([O-])(=O)C.[NH4+].C([BH3-])#[N:22].[Na+].CO>O>[Cl:15][C:10]1[CH:9]=[C:8]([C:4]2([CH:1]([NH2:22])[CH3:2])[CH2:7][CH2:6][CH2:5]2)[CH:13]=[CH:12][C:11]=1[Cl:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 130831391-Acetyl-1-(3,4-dichlorophenyl)cyclobutane

Product 1

HCID 130831401-[1-(3,4-Dichlorophenyl)cyclobutyl]ethylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-acetyl-1-(3,4-dichlorophenyl)cyclobutane (2.2 g) prepared as described in Example 1, ammonium acetate (7 g), sodium cyanoborohydride (0.4 g) and methanol (28 ml) was stirred at room temperature for four days. The reaction mixture was poured into a mixture of ice and water and the resulting mixture extracted with ether. The ether extract was washed with water, dried and the ether removed to leave 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine as an oil which was identified by standard analytical techniques as the compound of Example 1 in the form of its free base.

Workup

  1. customprepared
  2. extractionthe resulting mixture extracted with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. customdried
  6. customthe ether removed

Sources & evidence

ORD record
ord-7674bef5d9e041ee8f973cdc24c65f62
Source dataset
uspto-grants-1985_06
Patent number
US04522828

Reaction notes

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