Propanal → HCID 44181558, compound

HRID 415351Notes

Reaction equation

HRID 415351 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][C:15]4[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH:25](=O)[CH2:26][CH3:27].[H][H]>CO.[Pd]>[CH2:25]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][C:15]4[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1)[CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 527PropanalHCID 66621492HCID 66621492, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44181558HCID 44181558, compoundYield 23.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(4-(piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide (200 mg, 0.62 mmol), 10% Pd/C (50 mg) and propanal (0.8 mL, 1.86 mmol) in methanol (20 mL) was purged with hydrogen at room temperature overnight. The solution was filtered and the filtrate was concentrated, the residue was purified by prep-HPLC to give 2-(4-(1-propylpiperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide (53 mg, yield 23%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 1.01 (s, 3H), 1.79 (s, 2H), 2.03-2.09 (m, 4H), 3.31-3.34 (m, 2H), 3.67 (s, 2H), 7.30-7.41 (m, 3H), 7.83 (s, 2H), 8.16 (s, 2H); LC-MS (ESI) m/z: 364 (M+1)+.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-9a5c4fffd96543fab826697b440f2e81
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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