1-Methylpiperazine → N-Desethyl-N-Methyl Vardenafil

HRID 2180993Notes

Reaction equation

HRID 2180993 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:14]1[NH:19][C:18](=[O:20])[C:17]2=[C:21]([CH3:27])[N:22]=[C:23]([CH2:24][CH2:25][CH3:26])[N:16]2[N:15]=1)[CH3:2].[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:32]2[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]2)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:14]1[NH:19][C:18](=[O:20])[C:17]2=[C:21]([CH3:27])[N:22]=[C:23]([CH2:24][CH2:25][CH3:26])[N:16]2[N:15]=1)[CH3:2]

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 1354301594-Ethoxy-3-(5-methyl-4-oxo-7-propyl-1,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl)benzene-1-sulfonyl chloride

Product 1

HCID 135544141N-Desethyl-N-Methyl VardenafilYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.23 g (3 mmol) of 4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo[5,1-f][1,2,4]triazin-2-yl)-benzenesulphonyl chloride are dissolved in 40 ml of dichloromethane and cooled to 0° C. After addition of a spatula tip of DMAP, 0.90 g (9.00 mmol) of N-methylpiperazine are added, and the reaction mixture is stirred at room temperature overnight. The mixture is diluted with dichloromethane, the organic phase is washed twice with water and dried over sodium sulphate and the solvent is removed under reduced pressure. Crystallization from ether gives 1.25 g (88%) of a colourless solid.

Workup

  1. additionare added
  2. washthe organic phase is washed twice with water
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed under reduced pressure
  5. customCrystallization from ether

Sources & evidence

ORD record
ord-687a061edd514733aa1e68e40dbc85df
Source dataset
uspto-grants-2005_05
Patent number
US06890922B2

Reaction notes

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