Dicyclohexylcarbodiimide → 2-(6-Methylpyridin-2-yl)ethan-1-amine

HRID 1090957Notes

Reaction equation

HRID 1090957 reaction equation
O[N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2N=N1.[CH:11]1([N:17]=C=NC2CCCCC2)CCCC[CH2:12]1.CS(NC1C=CC(C(=O)CCC(O)=O)=CC=1)(=O)=O>CN(C)C=O>[CH3:12][C:11]1[N:17]=[C:8]([CH2:7][CH2:6][NH2:2])[CH:9]=[CH:10][CH:5]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 113692744-(4-(Methylsulfonamido)phenyl)-4-oxobutanoic acid

Product 1

HCID 15141652-(6-Methylpyridin-2-yl)ethan-1-amineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.76 g (35.3 mmol) of 1-hydroxybenzotriazole and 7.27 g (35.3 mmol) of dicyclohexylcarbodiimide were added to a solution of 7.02 g (29.4 mmol) of 4-(4-methylsulfonylaminophenyl)-4-oxobutyric acid in 60 ml of dimethylformamide at 0° C. and the mixture was stirred at that temperature for 1 h. 4.80 g (35.3 mmol) of 2-(6-methyl-2-pyridyl)ethylamine obtained in the above step (2) was added thereto. The mixture was stirred at room temperature for 12 h and then filtered. The filtrate was concentrated. The solid residue thus obtained was washed with a solvent mixture of chloroform/acetic acid/ethanol to give 9.39 g (yield: 89%) of the intended compound in the form of white crystals.

Sources & evidence

ORD record
ord-cea46fe28e714476b41fcfee14149593
Source dataset
uspto-grants-1992_01
Patent number
US05082850

Reaction notes

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