HCID 21327436, compound → HCID 21327426, compound

HRID 597731Notes

Reaction equation

HRID 597731 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:6]=[C:7]([CH2:11][CH:12]([NH:14][C:15](=[O:25])[CH2:16][NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:13])[CH:8]=[CH:9][CH:10]=1)([O-])=O>CO.[Ni]>[ClH:1].[NH2:2][C:5]1[CH:6]=[C:7]([CH2:11][CH:12]([NH:14][C:15](=[O:25])[CH2:16][NH:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:13])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 21327436HCID 21327436, compound

Product 1

HCID 21327426HCID 21327426, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

7.5 gm of chloroacetyl chloride were added dropwise to a mixture of 18 gm of 1-(3'-nitro-phenyl)-2-amino-propane, 14 gm of potassium carbonate and 150 ml of acetonitrile, whereby the temperature of the mixture rose to 45° C, and the resulting mixture was refluxed for two hours. Thereafter, the reaction mixture was allowed to cool, and then it was diluted with ice water, whereupon 1-(3'-nitro-phenyl)-2-(chloroacetyl-amino)-propane (m.p. 118° -120° C, recrystallized from ethyl acetate/petroleum ether) crystallized out. 17 gm of this compound were added to a mixture of 14 gm of benzylamine and 200 ml of acetonitrile, and the mixture was refluxed for two hours. Thereafter, the benzylamine hydrochloride which had precipitated out was removed by suction filtration, the filtrate was acidified with ethereal hydrochloric acid, and the crystalline precipitate formed thereby was recrystallized from 1 N hydrochloric acid, yielding 11.5 gm of 1-(3'-nitro-phenyl)-2-(benzylaminoacetyl-amino)-propane hydrochloride, m.p. 167° -170° C. This hydrochloride was hydrogenated in methanol in the presence of Raney nickel at atmospheric pressure and room temperature, yielding 1-(3'-aminophenyl)-2-(benzylaminoacetyl-amino)-propane hydrochloride which was dissolved in ethanol, and the solution was admixed with the calculated amount of ethereal hydrochloric acid, yielding the dihydrochloride of the formula ##STR28## which had a melting point of 234° -236° C (decomp.).

Sources & evidence

ORD record
ord-4e4d25da727c4c7d872ad8fc91e90343
Source dataset
uspto-grants-1977_03
Patent number
US04015011

Reaction notes

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