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

HRID 1014270Notes

Reaction equation

HRID 1014270 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 (Intermediate B120, 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. 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 1-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-[2-(methylsulfonyl)ethyl]piperazine (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-4f618e4ea3864553952ff2fa14241507
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…