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

HRID 1492234Notes

Reaction equation

HRID 1492234 reaction equation
I.CS[C:4](=[NH:18])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[CH3:19][NH:20][CH3:21]>C(O)C>[CH3:19][N:20]([CH3:21])[C:4]([NH2:18])=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 178503978HCID 178503978, compound

Product 1

HCID 98854071,1-Dimethyl-2-(2-morpholinophenyl)guanidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 2-methyl-1-(2-morpholinophenyl)-2-thiopseudourea hydroiodide (1 g), dimethylamine (1 ml of a 33% solution in ethanol) and ethanol (2 ml) was kept at ambient temperature for 48 days. The mixture was then cooled in an ice bath. The resulting solid was separated by filtration, treated with dilute aqueous sodium hydroxide solution (5 ml) and the resulting mixture extracted with dichloromethane (2×50 ml). The extract was washed with brine, dried and the solvent removed by evaporation to give 1,1-dimethyl-2-(2-morpholinophenyl)guanidine (m.p. 143°-144° C.) which was recrystallised from hexane.

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. customThe resulting solid was separated by filtration
  3. additiontreated with dilute aqueous sodium hydroxide solution (5 ml)
  4. extractionthe resulting mixture extracted with dichloromethane (2×50 ml)
  5. washThe extract was washed with brine
  6. customdried
  7. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-67e7f2b7501747a6851c57bdc98c64bd
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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