Sodium Hydroxide → 2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide

HRID 1515391Notes

Reaction equation

HRID 1515391 reaction equation
[CH3:1][CH2:2][N:3]([C:6]([C:8]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]([CH2:11][NH2:12])[CH2:9]1)=[O:7])[CH2:4][CH3:5].Cl.Cl.[OH-].[Na+]>ClCCl>[CH3:5][CH2:4][N:3]([C:6]([C:8]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]([CH2:11][NH2:12])[CH2:9]1)=[O:7])[CH2:2][CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70695551HCID 70695551, compound

Product 1

HCID 116229092-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.000 g (3.53 mmol) of racemic milnacipran hydrochloride is suspended in the mixture of 10 ml of aqueous solution and 10 ml of dichlormethane, and 10% sodium hydroxide aqueous solution is added under stirring until the aqueous phase is basic (pH=11). The organic phases is separated, the aqueous phase is extracted with dichlormethane (8 ml every time) three times, the organic extracts are combined, washed two times with saturated salt water, then dried with anhydrous sodium sulfate, filtered and removed dichlormethane by distillation to give racemic milnacipran freebase. The racemic milnacipran freebase obtained and 1.420 g (3.53 mmol) of the group T1 of D-resolving agents are dissolved in 45 ml of 98% acetone-water respectively, mixed and crystallized, filtered to afford 1.054 g of resolved product formed by (+)-milnacipran and the group T1 of D-resolving agents, 80.1% yield, the optical purity of (+)-milnacipran contained in which is 98.5% e.e.

Workup

  1. additionis added
  2. customThe organic phases is separated
  3. extractionthe aqueous phase is extracted with dichlormethane (8 ml every time) three times
  4. washwashed two times with saturated salt water
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customremoved dichlormethane
  8. distillationby distillation

Sources & evidence

ORD record
ord-8cb27dcd7ec64e18b9f5f38e8554ebd4
Source dataset
uspto-grants-2012_07
Patent number
US08222454B2

Reaction notes

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