Styrene → Tranylcypromine

HRID 1657620Notes

Reaction equation

HRID 1657620 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+:9](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>>[C:3]1([CH:2]2[CH2:12][CH:11]2[NH2:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:3]1([CH:2]2[CH2:1][CH:11]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7501StyreneHCID 12192Ethyl diazoacetate

Product 2

HCID 5530TranylcypromineHCID 316914Ethyl 2-phenylcyclopropane-1-carboxylate

Procedure

Generally, the trans isomer of 2-phenylcyclopropylamine is prepared by reacting styrene with ethyl diazoacetate and forming the ester, ethyl 2-phenylcyclopropanecarboxylate. The resulting ester is hydrolyzed to the 2-phenylcyclopropanecarboxylic acid. At this stage there are 3 to 4 parts of the trans isomer to 1 part of the cis isomer. A complete separation is accomplished by recrystallizing the acid from hot water. The pure trans isomer comes out as crystalline material while the cis isomer stays in solution. The trans 2-phenylcyclopropanecarboxylic acid is then reacted with thionyl chloride to form the acid chloride which is then successively treated with sodium azide and subjected to the curtius degradation. The isocyanate formed by this procedure is hydrolyzed readily to the (+) (-) 2-phenylcyclopropylamine.

Sources & evidence

ORD record
ord-facebd36857b4cb086ef49139b1c6e8b
Source dataset
uspto-grants-1976_06
Patent number
US03961073

Reaction notes

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