Sodium Carbonate → 1-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-[2-(methylsulfonyl)ethyl]piperazine

HRID 419369Notes

Reaction equation

HRID 419369 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].O1CCOCC1.[CH:30]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH2:31].C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[CH2:19][CH2:20][N:21]([CH2:31][CH2:30][S:32]([CH3:35])(=[O:34])=[O:33])[CH2:22][CH2:23]3)[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 19354Methyl vinyl sulfoneHCID 312751,4-DioxaneHCID 598602641-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

Product 1

HCID 598602741-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-[2-(methylsulfonyl)ethyl]piperazineYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (Example 57, step C) (10.0 g, 23.27 mmol) and 1,4-dioxane (400 mL) was added MeOH (˜100 mL) to enhance solubility. Methyl vinyl sulfone (6.1 mL, 69.8 mmol) and Na2CO3 (7.4 g, 69.8 mmol) were added and the resultant mixture was heated at 80° C. overnight (˜16 h). LCMS indicated that the reaction had gone to completion. The solvent was evaporated and the residue was taken up in DCM (300 mL) and filtered to remove salts. The filtrate was concentrated in vacuo to afford the title compound of step A (9.9 g, >95%) which was carried forward with no further purification. MS (ES+, m/z) 427 (M+1).

Workup

  1. customThe solvent was evaporated
  2. filtrationfiltered
  3. customto remove salts
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c78d686d2e4b48ca923b7580fc38dc53
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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