3-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamine → 1-Amino-2-[3-(3-dimethylaminomethylphenoxy)propylamino]cyclobutene-3,4-dion

HRID 370540Notes

Reaction equation

HRID 370540 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[O:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH3:3].[NH2:16][C:17]1[C:20](=[O:21])[C:19](=[O:22])[C:18]=1OC>CO>[NH2:16][C:17]1[C:20](=[O:21])[C:19](=[O:22])[C:18]=1[NH:12][CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:13]=[CH:14][CH:15]=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH:6]=1

Participants

4

Reactant 2

HCID 129139503-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamineHCID 134522053-Amino-4-methoxycyclobut-3-ene-1,2-dione

Product 1

HCID 133886501-Amino-2-[3-(3-dimethylaminomethylphenoxy)propylamino]cyclobutene-3,4-dionYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(3-dimethylaminomethylphenoxy)propylamine (1.41 g; 6.77 mmoles) [prepared according to the procedure described in Belgian Pat. No. 867,106] and 1-amino-2-methoxy-cyclobutene-3,4-dione (0.86 g; 6.77 mmoles) in 40 mL of methanol was stirred at ambient temperature for 20 hours and then filtered to give 1.95 g of the title compound.

Workup

  1. customprepared
  2. filtrationfiltered

Sources & evidence

ORD record
ord-9e2f7c13a2644fdba81f99e59b5e0ad7
Source dataset
uspto-grants-1985_07
Patent number
US04526973

Reaction notes

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