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

HRID 1382468Notes

Reaction equation

HRID 1382468 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-f4805b8b84cf45da9ee22f5a71f7cb89
Source dataset
uspto-grants-1989_02
Patent number
US04806570

Reaction notes

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