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

HRID 1588639Notes

Reaction equation

HRID 1588639 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 which 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 which 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-f480d38d2b3a46a28d19837d83feca03
Source dataset
uspto-grants-1993_06
Patent number
US05223498

Reaction notes

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