Methylamine → N-methyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine

HRID 1194452Notes

Reaction equation

[C:1]([C:4]1([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].C(C1(C2C=CC(Cl)=C(Cl)C=2)CCC1)(=O)C.[CH3:30][NH2:31].[H][H]>C(O)C.[Pt]=O>[CH3:30][NH:31][CH:1]([C:4]1([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

1Acetyl-1-(4-chlorophenyl)cyclobutane (61 g prepared in a similar manner to that described in Example 1 for 1-acetyl-1-(3,4-dichlorophenyl)cyclobutane, platinum oxide (0.75 g), 33% solution of methylamine in ethanol (60 g) and ethanol (30 ml) were charged into an autoclave. The autoclave was filled with hydrogen and maintained at about 60° C. and 20 bar pressure for ten hours. The reaction mixture was filtered through charcoal and the solids washed with absolute alcohol. The solvents were removed by evaporation and a sample of the residue (10 g) was shaken with 2M hydrochloric acid (50 ml) and ether (50 ml). The aqueous layer was basified and extracted with ether. The ether extract yielded a liquid on evaporation which was distilled (109° C./0.3 mm Hg) to give N-methyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine (Formula I R1 =Me; R2 =H; R3 =Me; R4 =H; R5 =4-Cl and R6 =H).

Workup

additionwere charged into an autoclave
wait20 bar pressure for ten hours
filtrationThe reaction mixture was filtered through charcoal
washthe solids washed with absolute alcohol
customThe solvents were removed by evaporation
extractionextracted with ether
extractionThe ether extract
customyielded a liquid
customon evaporation which
distillationwas distilled (109° C./0.3 mm Hg)

Sources & evidence

ORD record: ord-7b1ad4225d5040a18f70a582ee2ac020
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04814352

Reaction notes

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