Sodium Hydroxide → Amlodipine

HRID 1840423Notes

Reaction equation

HRID 1840423 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].C1C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>ClCCl.O>[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 60496Amlodipine besylate

Product 1

HCID 2162AmlodipineYield 93.8%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

Amlodipine besylate (30 g) was slurried into a mixture of dichloromethane/water (1:1, 500 ml) and the rapidly slurred emulsion was basified to pH 11 with aqueous sodium hydroxide (5M). The resulting organic layer was separated and the remaining aqueous layer extracted with dichloromethane (100 ml). The combined extracts were washed with water (150 ml) dried (MgSO4) and evaporated in vacuo to afford an off-white solid (20.3 g).

Workup

  1. customThe resulting organic layer was separated
  2. extractionthe remaining aqueous layer extracted with dichloromethane (100 ml)
  3. washThe combined extracts were washed with water (150 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-51803a9efd024ddfb0e9ab5fa71acbc8
Source dataset
uspto-grants-2004_01
Patent number
US06680334B2

Reaction notes

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