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

HRID 1492278Notes

Reaction equation

HRID 1492278 reaction equation
O1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]#[N:15])CC1.[CH3:16][NH:17][CH3:18].[CH2:19]([OH:21])[CH3:20]>[OH-].[Na+]>[CH3:16][N:17]([CH3:18])[C:14]([NH2:15])=[N:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[N:4]1[CH2:5][CH2:6][O:21][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 702EthanolHCID 15746517N-(2-morpholinophenyl)cyanamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N-(2-morpholinophenyl)cyanamide (2 g) was heated under reflux with a 33% solution of dimethylamine in ethanol (15 ml) for 4 hours. The mixture was then cooled and the solvent removed by evaporation to give a residue which was suspended in 20% aqueous sodium hydroxide solution. The suspension was extracted with dichloromethane (3×25 ml) and the extracts were washed with water, and then brine, dried and evaporated to give 1,1-dimethyl-2-(2-morpholinophenyl) guanidine (m.p. 142°-143° C.) which was recrystallised from hexane.

Workup

  1. temperatureThe mixture was then cooled
  2. customthe solvent removed by evaporation
  3. customto give a residue which
  4. extractionThe suspension was extracted with dichloromethane (3×25 ml)
  5. washthe extracts were washed with water
  6. dry with materialbrine, dried
  7. customevaporated

Sources & evidence

ORD record
ord-377c0bcf4a81479093c12306351f5f97
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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