Acetonitrile → HCID 24882842, compound

HRID 1631698Notes

Reaction equation

HRID 1631698 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH3:30][C:31]#[N:32]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CCOC(C)=O>[NH2:32][CH2:31][CH2:30][N:21]1[CH2:22][CH2:23][CH:18]([N:4]([CH:1]2[CH2:3][CH2:2]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:6])=[O:7])[CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 24882842HCID 24882842, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

N-[1-(2-Aminoethyl)-piperidin-4-yl]-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide (114) was prepared as follows. A mixture of compound 19 (0.5 g, 1.4 mmol), compound 113 (160 mg, 1.3 mmol, Aldrich), K2CO3 (1.0 g, 7.2 mmol), KI (10 mg) and benzyltriethylammonium chloride (20 mg, 0.07 mmol, ACROS) in 4 mL of CH3CN was shaken at 60° C. for 24 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc (20 mL), washed with water (4 mL) and brine (4 mL), concentrated and purified by column (Silica gel, EtOAc/MeOH/NH4OH 100/10/1) to give the title compound 114 as a free base, which was converted to its HCl-salt by treating with 1N HCl and dried (HCl-salt, white solid, yield 30%): 1H NMR (400 MHz, CD3OD, HCl-salt): δ 8.22 (d, 1H, 7.9 Hz), 8.18 (s, 1H), 8.04 (d, 1H, 7.9 Hz), 7.88 (dd, 1H, 7.8 & 7.9 Hz), 4.24-4.31 (m, 1H), 3.69-4.73 (m, 2H), 3.44-3.47 (m, 4H), 3.2-3.26 (m, 2H), 2.45-2.59 (m, 2H), 2.08-2.11 (m, 1H), 1.88-1.92 (m, 2H), 0.95-0.98 (m, 2H), 0.85-0.88 (m, 2H); LC: 100%; MS: m/z=510 (M+1).

Workup

  1. customN-[1-(2-Aminoethyl)-piperidin-4-yl]-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide (114) was prepared
  2. temperatureAfter cooling to room temperature
  3. washwashed with water (4 mL) and brine (4 mL)
  4. concentrationconcentrated
  5. custompurified by column (Silica gel, EtOAc/MeOH/NH4OH 100/10/1)

Sources & evidence

ORD record
ord-98dc45a345a041f586aaf154229420c8
Source dataset
uspto-grants-2014_07
Patent number
US08791264B2

Reaction notes

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