Benzylamine → ethyl hexahydro-4-[(phenylmethyl)amino]-1H-azepine-1-carboxylate

HRID 704710Notes

Reaction equation

HRID 704710 reaction equation
O=[C:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1.[C:14]1([CH2:20][NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.S1C=CC=C1.[H][H]>CO.[Pd]>[C:14]1([CH2:20][NH:21][CH:2]2[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8030ThiopheneHCID 126660861-Carbethoxyazepan-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 15037322ethyl hexahydro-4-[(phenylmethyl)amino]-1H-azepine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 46 parts of ethyl hexahydro-4-oxo-1H-azepine-1-carboxylate, 26 parts of benzenemethanamine, 2 parts of a solution of thiophene in methanol 4% and 400 parts of methanol was hydrogenated 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 69.1 parts (100%) of ethyl hexahydro-4-[(phenylmethyl)amino]-1H-azepine-1-carboxylate as a residue (interm. 27).

Workup

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

Sources & evidence

ORD record
ord-5b4de34054044b898b5cfe2297e92abb
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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