Triethylamine → 1-(1-Methylpiperidin-4-yl)-4-((1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-2-yl)methylsulfonyl)piperazine

HRID 1643470Notes

Reaction equation

HRID 1643470 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[F:21][C:22]([F:44])([F:43])[C:23]1[CH:24]=[C:25]([S:29]([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]2[CH2:38][S:39](Cl)(=[O:41])=[O:40])(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1>C(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([N:8]2[CH2:13][CH2:12][N:11]([S:39]([CH2:38][CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37][N:32]3[S:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:44])([F:21])[F:43])[CH:24]=3)(=[O:31])=[O:30])(=[O:40])=[O:41])[CH2:10][CH2:9]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 59367748HCID 59367748, compound

Product 1

HCID 462049761-(1-Methylpiperidin-4-yl)-4-((1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-2-yl)methylsulfonyl)piperazineYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(1-Methyl-4-piperidinyl)piperazine (1.126 mmol) was dissolved in methylene chloride (7 ml), the solution was cooled in an ice bath and triethylamine (2.8 mmol) and (1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-2-yl)methanesulfonic acid chloride (dissolved in methylene chloride (3 ml)) were added. The mixture was stirred for 16 h, during which it was allowed to warm slowly to room temperature. The reaction mixture was diluted with methylene chloride and washed with water and the organic phase was dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with methylene chloride/methanol (19:1). Yield: 30%. MS, Rt=2.4 min, m/z=553.0 [MH]+

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. washwashed with water
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel) with methylene chloride/methanol (19:1)

Sources & evidence

ORD record
ord-64b94bdc6da8478e9d722c226b99b3b0
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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