Water → Amlodipine

HRID 2180022Notes

Reaction equation

HRID 2180022 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.O.[OH-].[Na+]>C(Cl)Cl>[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

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 60496Amlodipine besylate

Product 1

HCID 2162Amlodipine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slight suspension of racemic amlodipine besylate (100.37 g, 0.177 mol) [prepared by the method described in European Patent No. 0244944] in methylene chloride (250 mL, 2.5 mL/g) and water (250 mL, 2.5 mL/g) was added 11 M sodium hydroxide (24 mL) to achieve pH 13-14. The mixture was stirred for ten minutes during which time it became a solution. The layers were separated and the organic layer washed with water (1×250 mL) and gravity filtered through a magnesium sulphate (25 g) bed. The magnesium sulphate was washed with methylene chloride (40 mL) and to the combined filtrates was added dimethyl sulphoxide (360 mL). The methylene chloride was removed on a rotary evaporator (45 minutes on a water aspirator followed by 15 minutes under high vacuum).

Workup

  1. customprepared by the method
  2. customThe layers were separated
  3. washthe organic layer washed with water (1×250 mL) and gravity
  4. filtrationfiltered through a magnesium sulphate (25 g) bed
  5. washThe magnesium sulphate was washed with methylene chloride (40 mL) and to the combined filtrates
  6. additionwas added dimethyl sulphoxide (360 mL)
  7. customThe methylene chloride was removed on a rotary evaporator (45 minutes on a water

Sources & evidence

ORD record
ord-386b996615f54ca8883ab09216eaf25e
Source dataset
uspto-grants-2005_05
Patent number
US06887886B2

Reaction notes

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