Thiophene → ethyl 4-aminohexahydro-1H-azepine-1-carboxylate

HRID 2166119Notes

Reaction equation

HRID 2166119 reaction equation
C1(C[NH:8][CH:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10]2)C=CC=CC=1.S1C=CC=C1.[H][H]>CO.[Pd]>[NH2:8][CH:9]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 15037322ethyl hexahydro-4-[(phenylmethyl)amino]-1H-azepine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 15037323ethyl 4-aminohexahydro-1H-azepine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

69.1 Parts of ethyl hexahydro-4-[(phenylmethyl)amino]-1H-azepine-1-carboxylate were hydrogenated in the presence of a solution of thiophene in methanol 4% and methanol at normal pressure and at room temperature with 4 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 46.9 parts (100%) of ethyl 4-aminohexahydro-1H-azepine-1-carboxylate as a residue (interm. 3).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f9a8009ef6264252b77caa40f496e0d2
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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