Oxalic Acid → HCID 70430491, compound

HRID 1906656Notes

Reaction equation

HRID 1906656 reaction equation
CC([NH:9][CH:10]([CH3:23])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1)C1C=CC=CC=1.[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>CO.[Ni]>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[CH3:23][C@H:10]([NH2:9])[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:20])=[O:21])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 53748245HCID 53748245, compound

Product 1

HCID 70430491HCID 70430491, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

4-(4-Aminosulphonylphenyl)butanone-2 was reacted with (S)-(-)-α-phenylethylamine and p-toluenesulphonic acid as the catalyst in toluene with separation of water to give the Schiff's base (S)-N-(α-methylbenzyl)-1-methyl-3-(4-aminosulphonylphenyl)propylimine. The imine was hydrogenated in methanol in the presence of Raney-nickel to give a mixture of the optical isomers of N-(α-methylbenzyl)-1-methyl-3-(4-aminosulphonylphenyl)propylamine. The amine was converted with oxalic acid into a mixture of the oxalates from which there was obtained by two-fold crystallization pure (S)-1-methyl-3-(4-aminosulphonylphenyl)propylamine oxalate of melting point 123°-127°, [α]D20 =-68° (c=1.0 in methanol). Hydrogenolysis of this substance in alcohol under 4 bar of hydrogen at 60° for 24 hours yielded pure (S)-1-methyl-3-(4-aminosulphonylphenyl)propylamine.

Workup

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Sources & evidence

ORD record
ord-c017cea4d0ee4378b7e0202ae381ea6d
Source dataset
uspto-grants-1987_03
Patent number
US04652679

Reaction notes

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