M-Cresol → 1,1-Dimethyl-2-(2-morpholinophenyl)guanidine

HRID 1492297Notes

Reaction equation

HRID 1492297 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[NH2:10])[CH2:4][CH2:3]1.C1C(O)=CC=CC=1C.[CH3:23][N:24]([CH3:27])[C:25]#[N:26].[OH-].[Na+]>O>[CH3:23][N:24]([CH3:27])[C:25]([NH2:26])=[N:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[N:5]1[CH2:4][CH2:3][O:2][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 342M-CresolHCID 14798Sodium HydroxideHCID 15112DimethylcyanamideHCID 189522842-Morpholinoaniline hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-morpholinoaniline hydrochloride (19.2 g), m-cresol (80 ml) and dimethylcyanamide (9.45 g) was heated at 100° C. for five hours, cooled and added to a mixture of 40% aqueous sodium hydroxide solution (300 ml) and ice (300 g). Water (300 ml) was added and the resulting solid separated by filtration, washed with water and dissolved in dichloromethane. The solution was dried and the solvent removed to give a residue which was recrystallised from hexane to give 1,1-dimethyl-2-(2-morpholinophenyl)guanidine (m.p. 142°-143° C.).

Workup

  1. temperaturecooled
  2. customthe resulting solid separated by filtration
  3. washwashed with water
  4. dissolutiondissolved in dichloromethane
  5. customThe solution was dried
  6. customthe solvent removed
  7. customto give a residue which
  8. customwas recrystallised from hexane

Sources & evidence

ORD record
ord-e90bfb3dfc08457cbc532ea32c3f3988
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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