Triethylamine → N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamide

HRID 1428952

Reaction equation

HRID 1428952 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:28]2[CH2:30][CH2:29]2)[S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)(=[O:17])=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCC(NC2CC2)CC1)C1C=CC=CC=1.C(N(CC)CC)C.FC(F)(F)C1C=C(S(Cl)(=O)=O)C=CC=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH:28]1([N:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)(=[O:16])=[O:17])[CH2:30][CH2:29]1.[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:28]2[CH2:30][CH2:29]2)[S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[CH:19]=2)(=[O:16])=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 27354811-Benzyl-N-cyclopropylpiperidin-4-amineHCID 4114155N-(1-benzylpiperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide

Product 2

HCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamideHCID 4114155N-(1-benzylpiperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(1-Benzylpiperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide: N-Benzyl-4-cyclopropylaminopiperidine (5.0 g, 21.71 mmol) and triethylamine (3.6 mL, 26.05 mmol) were dissolved in dichloromethane (DCM, 100 mL). 3-Trifluoromethylbenzenesulfonyl chloride (3.47 mL, 21.71 mmol) was added and the resulting reaction mixture was stirred overnight. The mixture then was poured into potassium carbonate solution (200 mL), extracted with ether (2×200 mL), dried (MgSO4), and concentrated in vacuum to give a crude product as a yellow gum, which was purified by column chromatography on silica gel (hexane/EtOAc, 2:1). The title compound N-(1-benzylpiperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide was obtained (9 g, 95% yield) as a pale yellow gum. Rf=0.42 (UV detection).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with ether (2×200 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuum
  5. customto give a crude product as a yellow gum, which
  6. customwas purified by column chromatography on silica gel (hexane/EtOAc, 2:1)

Sources & evidence

ORD record
ord-1f6641ea8fe248938efe7100e90267a5
Source dataset
uspto-grants-2015_01
Patent number
US08937181B2

Linked notes

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