1-(Allyl)pyrrolidine-2-methylamine → N-(1-allyl-2-pyrrolidylmethyl)-7-methylsulfamoyl-1,4-benzodioxane-5-carboxamide

HRID 2052633Notes

Reaction equation

HRID 2052633 reaction equation
[CH2:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][NH2:10])[CH:2]=[CH2:3].[CH3:11][NH:12][S:13]([C:16]1[CH:17]=[C:18]([C:26](Cl)=[O:27])[C:19]2[O:24][CH2:23][CH2:22][O:21][C:20]=2[CH:25]=1)(=[O:15])=[O:14]>>[CH2:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][NH:10][C:26]([C:18]1[C:19]2[O:24][CH2:23][CH2:22][O:21][C:20]=2[CH:25]=[C:16]([S:13](=[O:15])(=[O:14])[NH:12][CH3:11])[CH:17]=1)=[O:27])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 1172961-(Allyl)pyrrolidine-2-methylamineHCID 205447207-Methylsulfamoyl-1,4-benzodioxane-5-carbonyl chloride

Product 1

HCID 24834937N-(1-allyl-2-pyrrolidylmethyl)-7-methylsulfamoyl-1,4-benzodioxane-5-carboxamideYield 52.6%

Procedure

In a similar manner to the above example, 84 g of dextrorotatory 1-allyl-2-aminomethyl-pyrrolidine was reacted with 175 g of 7-methylsulfamoyl-1,4-benzodioxane-5-carbonyl chloride to give, after purification, 125 g of dextrorotatory-N-(1-allyl-2-pyrrolidylmethyl)-7-methylsulfamoyl-1,4-benzodioxane-5-carboxamide (M.P.: 104°-105° C.; yield: 52.6%).

Workup

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Sources & evidence

ORD record
ord-6717da927fbf4648b1fc162dba139651
Source dataset
uspto-grants-1980_01
Patent number
US04186135

Reaction notes

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