Phosphorus oxychloride → N-methyl-N'-(2-morpholinomethylphenyl)pivalamidine monofumarate

HRID 1588602Notes

Reaction equation

HRID 1588602 reaction equation
[CH3:1][NH:2][C:3](=O)[C:4]([CH3:7])([CH3:6])[CH3:5].[NH2:9][C:10]1[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=1[CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.P(Cl)(Cl)(Cl)=O.[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C1C=CC=CC=1.CO>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[CH3:1][NH:2][C:3](=[N:9][C:10]1[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=1[CH2:12][N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)[C:4]([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 138844N,2,2-TrimethylpropanamideHCID 444972Fumaric AcidHCID 64845552-(Morpholin-4-ylmethyl)aniline

Product 1

HCID 178484900N-methyl-N'-(2-morpholinomethylphenyl)pivalamidine monofumarate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 887MethanolSolvent

Procedure

A mixture of N-methylpivalamide (6.2 g) in benzene (50 ml), 4-(2-aminobenzyl)morpholine (9 g) in benzene (40 ml) and phosphorus oxychloride (5 ml) was heated at 80°-85° C. for 12 hours to yield a solid which was dissolved in methanol (25 ml) and treated with fumaric acid (1.4 g) to give N-methyl-N'-(2-morpholinomethylphenyl)pivalamidine monofumarate (m.p. 167°-168° C.) which was recrystallised from propan-2-ol.

Workup

  1. customto yield a solid which

Sources & evidence

ORD record
ord-041b230cf06d42c79af9d693f88a74ed
Source dataset
uspto-grants-1993_06
Patent number
US05223498

Reaction notes

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