Acetic Acid → HCID 178476642, compound

HRID 45296

Reaction equation

HRID 45296 reaction equation
[CH3:1][N:2]([C:4]([NH:6][C:7]([NH2:9])=[NH:8])=[NH:5])[CH3:3].[C:10]([OH:13])(=[O:12])[CH3:11]>CC(C)=O>[CH3:1][N:2]([C:4]([NH:6][C:7]([NH2:9])=[NH:8])=[NH:5])[CH3:3].[C:10]([O-:13])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 178484382HCID 178484382, compound

Product 1

HCID 178476642HCID 178476642, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2 kg (1 equivalent) of metformin hydrochloride and 483 g (1 equivalent) of sodium hydroxide were stirred in 10 L of methanol for 2 hours at room temperature, and then remaining solid was filtered and the filtrate was concentrated under reduced pressure. Then 15 L of acetone was added to the resulting solid and stirred. Insoluble material was filtered, and the filtrate was concentrated under reduced pressure to obtain 1,230 g of metformin free base. The metformin free base was dissolved in 33 L of acetone, 2.8 L (4 equivalents) of acetic acid was added, and then the mixture was stirred for 2 hours at room temperature. The resulting crystal was filtered, and re-crystallized in water and acetone to obtain 1,089 g of metformin acetate (yield: 47.7%).

Workup

  1. filtrationThe resulting crystal was filtered
  2. customre-crystallized in water

Sources & evidence

ORD record
ord-1d4ddea1485044f8bf175bad0b24f4a1
Source dataset
uspto-grants-2013_09
Patent number
US08541474B2

Linked notes

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