Hydrochloric Acid → N-(1-ethyl-2-pyrrolidylmethyl)-8-amino-1,4-benzodioxane-5-carboxamide dihydrochloride

HRID 2052655Notes

Reaction equation

HRID 2052655 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]([C:12]([OH:14])=O)=[CH:4][CH:3]=1.[CH2:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[CH2:22][NH2:23])[CH3:16].[ClH:24]>CO>[ClH:24].[ClH:24].[CH2:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[CH2:22][NH:23][C:12]([C:5]1[C:6]2[O:11][CH2:10][CH2:9][O:8][C:7]=2[C:2]([NH2:1])=[CH:3][CH:4]=1)=[O:14])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 211934708-Amino-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

Product 1

HCID 70548321N-(1-ethyl-2-pyrrolidylmethyl)-8-amino-1,4-benzodioxane-5-carboxamide dihydrochlorideYield 72.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the method described in Example 2, 42 g of 8-amino-1,4-benzodioxane-5-carboxylic acid were treated with methanol and the resulting compound treated with 33 g of 1-ethyl-2-aminomethylpyrrolidine and then with a solution of 13 g of hydrochloric acid in absolute alcohol. 49 g of N-(1-ethyl-2-pyrrolidylmethyl)-8-amino-1,4-benzodioxane-5-carboxamide dihydrochloride were obtained (M.P.: 173° C.; yield: 60%).

Sources & evidence

ORD record
ord-0629b08b1ad14ab99227c2acf11f180e
Source dataset
uspto-grants-1980_01
Patent number
US04186135

Reaction notes

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