Dimethylamine → 1,1-Dimethyl-2-(5-chloro-2-morpholinophenyl)guanidine

HRID 1492282Notes

Reaction equation

HRID 1492282 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH2:16][CH2:15]OCC2)=[C:6]([NH:8][C:9]#[N:10])[CH:7]=1.[CH3:17][NH:18][CH3:19].[CH2:20]([OH:22])[CH3:21]>>[CH3:17][N:18]([CH3:19])[C:9]([NH2:10])=[N:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N:11]1[CH2:16][CH2:15][O:22][CH2:20][CH2:21]1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 702EthanolHCID 18952323HCID 18952323, compound

Product 1

HCID 189521321,1-Dimethyl-2-(5-chloro-2-morpholinophenyl)guanidine

Procedure

In a similar manner to that described in Example 272, N-(5-chloro-2-morpholinophenyl)cyanamide (2.3 g) in ethanol (10 ml) and a 33% ethanolic solution of dimethylamine (6 ml) were heated under reflux for 4 hours to give 1,1-dimethyl-2-(5-chloro-2-morpholinophenyl)guanidine (m.p. 135°-138° C.) which was recrystallised from hexane and then was converted into its monofumarate salt (m.p. 223°-225° C.) which was recrystallised from methanol.

Workup

  1. temperatureunder reflux for 4 hours

Sources & evidence

ORD record
ord-7df32efa294f4e0da2308624f7d01737
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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