Metformin Hydrochloride → 1,3,5-Triazine-2,4-diamine, 3,6-dihydro-N2,N2,6-trimethyl-, hydrochloride (1:1)

HRID 1256936Notes

Reaction equation

HRID 1256936 reaction equation
[CH3:1][N:2]([C:4]([N:6]=[C:7]([NH2:9])[NH2:8])=[NH:5])[CH3:3].[ClH:10].[CH3:11][CH:12]1OC(C)OC(C)O1>C(O)C(C)C>[ClH:10].[NH2:8][C:7]1[NH:6][C:4]([N:2]([CH3:3])[CH3:1])=[N:5][CH:11]([CH3:12])[N:9]=1

Participants

4

Reactant 2

HCID 14219Metformin HydrochlorideHCID 31264Paraldehyde

Product 1

HCID 101764861,3,5-Triazine-2,4-diamine, 3,6-dihydro-N2,N2,6-trimethyl-, hydrochloride (1:1)Yield 176.6%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Conditions

Temperature
12.5 °C

Procedure

A mixture of 100.1 g of metformin hydrochloride, 36.5 g of paraldehyde and 4 g of Dowex DR-2030 in 237.8 ml of isobutanol is heated under reflux for 6 hours. The catalyst is subsequently filtered off, and some of the solvent is removed by distillation. The remainder of the solution is cooled to 10-15° C., and the white precipitate is separated off, giving 93.5 g (80.7%) of 4-amino-3,6-dihydro-2-dimethylamino-6-methyl-1,3,5-triazine hydrochloride.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. filtrationThe catalyst is subsequently filtered off
  4. customsome of the solvent is removed by distillation
  5. customthe white precipitate is separated off

Sources & evidence

ORD record
ord-53773af7f5b94d45bb157aefc7973fd1
Source dataset
uspto-grants-2013_06
Patent number
US08461331B2

Reaction notes

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