Reaction #73575

ord-dec2cd9c4d9a4b31a41e029463ef90e6

Reaction equation

CN(C)C(=N)N=C(N)N.Cl
metformin hydrochloride
[Na+].[OH-]
sodium hydroxide
CC(=O)O
acetic acid
CC(=O)[O-].CN(C)C(=N)NC(=N)N
metformin acetate
Yield 48.7%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGthe mixture was stirred overnight at room temperature
  2. 2
    WashThe resulting crystal was washed with acetone-water (12:1) mixture
  3. 3
    Dryingacetone, and dried at 60° C.

Procedure

5 L of water, 2 kg (1 equivalent) of metformin hydrochloride and 578 g (1.2 equivalents) of sodium hydroxide were added to 10 L reactor, and stirred for 2 hours at room temperature. Then 1 L (1.45 equivalents) of acetic acid was added for 1 hour, and the mixture was stirred overnight at room temperature. The resulting crystal was washed with acetone-water (12:1) mixture, and then acetone, and dried at 60° C. to obtain 1,112 g of metformin acetate (yield: 48.7%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08541474B2uspto-grants-2013_09