Acetic Acid → HCID 11525806, compound

HRID 2054171Notes

Reaction equation

HRID 2054171 reaction equation
[CH3:1][CH:2]([CH3:19])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:7]=1)=[O:4].[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27][C:28]2[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=2)=[CH:23][CH:22]=1.C(O)(=O)C.[Na].C([O-])(O)=O.[Na+]>ClC(Cl)C.C1CCCCC1.CCOC(C)=O.C(Cl)Cl>[F:20][C:21]1[CH:22]=[CH:23][C:24]([S:27][C:28]2[CH:35]=[CH:34][C:31]([CH2:32][N:16]3[CH2:17][CH2:18][CH:13]([C:8]4[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH:2]([CH3:19])[CH3:1])[CH:11]=[CH:10][C:9]=4[CH3:12])[CH2:14][CH2:15]3)=[CH:30][CH:29]=2)=[CH:25][CH:26]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 10561543HCID 10561543, compoundHCID 167572542-Methyl-N-[4-methyl-3-(4-piperidinyl)phenyl]propanamide

Product 1

HCID 11525806HCID 11525806, compoundYield 36.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

2-methyl-N-(4-methyl-3-(4-piperidyl)phenyl)propanamide (130 mg, 0.500 mmol) and 4-(4-fluorophenylthio)benzaldehyde (116 mg, 0.500 mmol) were dissolved in dichloroethane (5.00 mL) and acetic acid (30.0 mg, 0.500 mmol), and sodium triacetoxborohydride (212 mg, 1.00 mmol) was added at room temperature. Stirring was continued under nitrogen at room temperature for 10 h, then a saturated aqueous NaHCO3 solution and CH2Cl2 was added. The phases were separated, and the organic phase was washed with water, dried over Na2SO4 and concentrated in vacuo. Purification by flash column chromatography (eluent: cyclohexane:EtOAc (85:15 then 7:3)) gave N-[3-(1-{[4-(4-fluorophenylthio)phenyl]methyl}(4-piperidyl))-4-methylphenyl]-2-methylpropanamide (86.3 mg, 36.2% yield) as a white solid. 1H NMR (CDCl3) δ 7.43-7.32 (m, 3H), 7.31-7.22 (m, 5H), 7.09-6.98 (m, 4H), 3.51 (s, 2H), 3.04-2.93 (m, 2H), 2.76-2.61 (m, 1H), 2.52-2.41 (m, 1H), 2.27 (s, 3H), 2.14-2.03 (m, 2H), 1.86-1.65 (m, 4H), 1.25 (d, 6H, J=7.026 Hz); ESMS m/e: 477.2 (M+H)+.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash column chromatography (eluent

Sources & evidence

ORD record
ord-4814581855104ffaa31a686af1b80ac7
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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