Acetone → Sildenafil

HRID 1435822Notes

Reaction equation

HRID 1435822 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[OH-].[Na+].[CH3:10][N:11]1[C:19]2[C:18](=[O:20])[N:17]=[C:16]([C:21]3[C:22](C4C=CC(OCC)=CC=4)=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=3)[NH:15][C:14]=2[C:13]([CH2:40][CH2:41][CH3:42])=[N:12]1.[CH3:43][C:44](C)=[O:45]>>[CH3:42][CH2:41][CH2:40][C:13]1[C:14]2[N:15]=[C:16]([C:21]3[CH:22]=[C:23]([S:27]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)(=[O:29])=[O:28])[CH:24]=[CH:25][C:26]=3[O:45][CH2:44][CH3:43])[NH:17][C:18](=[O:20])[C:19]=2[N:11]([CH3:10])[N:12]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 178440326HCID 178440326, compound

Product 1

HCID 135398744SildenafilYield 87%

Conditions

Temperature
0 °C

Procedure

In a 3-necked flask, N-methyl piperazine (1.34 g, 13.4 mol) and NaOH (47%, 0.49 g) were mixed at room temperature. 3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-(4-ethoxyphenyl)benzene sulfonyl chloride (5 g, 12.2 mmol) was suspended in acetone (50 ml) and the suspension was added to the mixture of bases to form a reaction mixture. The reaction mixture was stirred for 45 mm, cooled to 0° C., and filtered. The collected precipitate was washed with water twice and dried at 50° C. under 10 mm Hg to yield pure sildenafil in 87% yield.

Workup

  1. additionthe suspension was added to the mixture of bases
  2. customto form a reaction mixture
  3. filtrationfiltered
  4. washThe collected precipitate was washed with water twice
  5. customdried at 50° C. under 10 mm Hg

Sources & evidence

ORD record
ord-16809ac42b4441b58ec8b9a2bc259640
Source dataset
uspto-grants-2009_11
Patent number
US07618976B2

Reaction notes

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