Acetic Acid → HCID 69115453, compound

HRID 2054169Notes

Reaction equation

HRID 2054169 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:4][C:3]=1[CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33][C:34]2[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=2)=[CH:29][CH:28]=1.ClC(Cl)C.C(O)(=O)C.[Na].C([O-])(O)=O.[Na+]>C1CCCCC1.CCOC(C)=O.C(Cl)Cl>[CH3:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([S:33][C:34]2[CH:41]=[CH:40][C:37]([CH2:38][N:22]3[CH2:21][CH2:20][CH:19]([C:3]4[CH:4]=[C:5]([NH:8][C:9]([O:11][CH2:12][C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)=[O:10])[CH:6]=[CH:7][C:2]=4[CH3:1])[CH2:24][CH2:23]3)=[CH:36][CH:35]=2)=[CH:31][CH:32]=1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 157278344-[(4-Methoxyphenyl)thio]benzaldehydeHCID 69115392HCID 69115392, compound

Product 1

HCID 69115453HCID 69115453, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

A mixture of N-(4-methyl-3-(4-piperidyl)phenyl)(phenylmethoxy)carboxamide (324 mg, 1.00 mmol) and 4-(4-methoxyphenylthio)benzaldehyde (244 mg, 1.00 mmol), dichloroethane (5.00 mL), acetic acid (60.0 mg, 1.00 mmol) and sodium triacetoxborohydride (424 mg, 2.00 mmol) was stirred under nitrogen at room temperature for 18 h. Saturated NaHCO3 solution and CH2Cl2 was added. The mixture was separated, and the organic layer was washed with water (10 mL), 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-methoxyphenylthio)phenyl]methyl}(4-piperidyl))-4-methylphenyl](phenylmethoxy) carboxamide (486 mg, 88.0% yield) as a white foam. ESMS m/e: 553.2 (M+H)+.

Workup

  1. customThe mixture was separated
  2. washthe organic layer was washed with water (10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash column chromatography (eluent

Sources & evidence

ORD record
ord-f288dc568a8749ba9ed8d6eff8cc85e6
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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