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Metformin Hydrochloride → HCID 178484382, compound

HRID 45295
Notes
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Reaction equation

HRID 45295 reaction equation
[CH3:1][N:2]([C:4]([N:6]=[C:7]([NH2:9])[NH2:8])=[NH:5])[CH3:3].Cl.[OH-].[Na+]>CO>[CH3:1][N:2]([C:4]([NH:6][C:7]([NH2:9])=[NH:8])=[NH:5])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14219Metformin HydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 178484382HCID 178484382, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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. filtrationwas filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThen 15 L of acetone was added to the resulting solid
  4. filtrationInsoluble material was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0d412acdfa6949519a58c094e4bf455b
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541474B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes