Propanal → 2-(1-Propylpiperidin-3-yl)benzo[d]oxazole-7-carboxamide

HRID 415338Notes

Reaction equation

HRID 415338 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[O:8][C:9]3[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:2]1.[CH:19](=O)[CH2:20][CH3:21].[H][H]>CO.[Pd]>[CH2:19]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[O:8][C:9]3[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:2]1)[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 527PropanalHCID 666209242-(Piperidin-3-yl)benzo[d]oxazole-7-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 441816762-(1-Propylpiperidin-3-yl)benzo[d]oxazole-7-carboxamideYield 52.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(piperidin-3-yl)benzo[d]oxazole-7-carboxamide (25 mg, 0.1 mmol), propionaldehyde (9 mg, 0.156 mmol) and 10% Pd/C (10 mg) in methanol (5 ml) was stirred at room temperature over 1 atm hydrogen for 3 h. Then the mixture solution was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by prep-HPLC to obtain 2-(1-propylpiperidin-3-yl)benzo[d]oxazole-7-carboxamide (15 mg, yield 41%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 0.88-0.93 (t, J=7.2 Hz, 3H), 1.51-1.61 (m, 2H), 1.72-1.91 (m, 4H), 2.07-2.13 (m, 1H), 2.24-2.27 (m, 1H), 2.38-2.43 (t, J=8 Hz, 2H), 2.91-2.94 (d, J=11.2 Hz, 1H), 3.29-3.35 (m, 2H), 6.26 (s, 1H), 7.0 (s, 1H), 7.41-7.45 (t, J=7.6 Hz, 1H), 7.85-7.87 (d, J=7.6 Hz, 1H), 8.06-8.08 (d, J=8 Hz, 1H). LC-MS (ESI) m/z: 288 (M+1)+.

Workup

  1. filtrationThen the mixture solution was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-cff7262b3e934e6bb9813028bbc47b03
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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