Methanesulfonyl chloride → 1-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine

HRID 419366Notes

Reaction equation

HRID 419366 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].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[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]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:22][CH2:23]3)[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 598602641-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

Product 1

HCID 598602451-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazineYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (Example 57, step C) (5.0 g, 11.6 mmol), methane sulfonyl chloride (1.4 mL, 17.5 mmol) and DCM (200 mL) was added TEA (80.1 mL, 58.2 mmol). The reaction was stirred at rt and monitored by TLC. After complete consumption of the starting material the clear yellow solution was concentrated onto silica gel and purified by chromatography to afford the title compound of step A as a yellow solid (3.54 g, 76%). 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=9.5 Hz, 1H), 6.57 (dd, J=9.2, 2.6 Hz, 1H), 6.48 (d, J=2.6 Hz, 1H), 4.09-4.00 (m, 2H), 3.89 (s, 3H), 3.10-3.03 (m, 4H), 2.99-2.90 (m, 2H), 2.84 (s, 3H), 2.61-2.52 (m, 5H), 1.85-1.77 (m, 2H), 1.50-1.37 (m, 2H).

Workup

  1. customAfter complete consumption of the starting material the clear yellow solution
  2. concentrationwas concentrated onto silica gel
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-de03ff5ef7ce4d00bc8d061a558ea14d
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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