Potassium Hydroxide → Deacetyldiltiazem

HRID 464243Notes

Reaction equation

HRID 464243 reaction equation
Cl.C([O:5][C@H:6]1[C:12](=[O:13])[N:11]([CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]=2[S:8][C@H:7]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=O)C.[OH-].[K+]>C(O)C>[CH3:18][N:16]([CH3:17])[CH2:15][CH2:14][N:11]1[C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]=2[S:8][C@@H:7]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[C@@H:6]([OH:5])[C:12]1=[O:13]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 62920Diltiazem Hydrochloride

Product 1

HCID 91638Deacetyldiltiazem

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30 Grams (0.0665 mole) of cis-(+)-3-acetoxy-2,3-dihydro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-1,5-benzothiazepine-4(5H)-one hydrochloride were added to a solution of 7.5 g (0.1337 mole) of potassium hydroxide in 450 ml of ethanol. The resulting mixture was kept at room temperature for 90 minutes, then the solvent was evaporated off in vacuo, the residue was taken up with water and subsequently extracted with CHCl3. The organic phase wase washed with water, in order to remove the excess of alkali, then dried over sodium sulfate. After evaporating the solvent under vacuum, 24.26 g of a glassy paste which became solid upon standing overnight at room temperature was obtained. It was finally ground and used as such for the subsequent reactions.

Workup

  1. customthe solvent was evaporated off in vacuo
  2. extractionsubsequently extracted with CHCl3
  3. washThe organic phase wase washed with water, in order
  4. customto remove the excess of alkali,
  5. dry with materialthen dried over sodium sulfate
  6. customAfter evaporating the solvent under vacuum, 24.26 g of a glassy paste which
  7. waitupon standing overnight at room temperature
  8. customwas obtained

Sources & evidence

ORD record
ord-689eea90cf83447ba40460ce5b847cdf
Source dataset
uspto-grants-1985_10
Patent number
US04547495

Reaction notes

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