Propanal → HCID 44181675, compound

HRID 415342Notes

Reaction equation

HRID 415342 reaction equation
[C:1]([C:4]1[C:12]2[O:11][C:10]([CH:13]3[CH2:18][CH2:17][N:16]([C:19](OCC4C=CC=CC=4)=O)[CH2:15][CH2:14]3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[CH:29](=O)[CH2:30]C.[H][H]>CO.[Pd]>[CH2:19]([N:16]1[CH2:15][CH2:14][CH:13]([C:10]2[O:11][C:12]3[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=[CH:7][C:8]=3[N:9]=2)[CH2:18][CH2:17]1)[CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 527PropanalHCID 66621374HCID 66621374, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44181675HCID 44181675, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (200 mg, 0.53 mmol), propionaldehyde (40 mg, 0.7 mmol) and 10% Pd/C (20 mg) in methanol (20 mL) was stirred at room temperature over 1 atm hydrogen for 4 hr. The mixture was filtered, and evaporated under reduced pressure. The residue was purified by prep-HPLC to give 2-(1-propylpiperidin-4-yl)benzo[d]oxazole-7-carboxamide (71 mg, yield 46%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.84-0.88 (t, J=7.2 Hz, 1H), 1.43-1.48 (m, 2H), 1.83-1.89 (m, 2H), 2.04-2.12 (m, 2H), 2.24-2.28 (m, 2H), 2.88-2.91 (m, 2H), 2.89-3.02 (m, 1H), 7.39-7.73 (t, J=7.6 Hz, 1H), 7.72-7.77 (m, 3H), 7.84-7.85 (d, J=6.8 Hz, 1H); LCMS (ESI) m/z: 288 (M+1)+.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated under reduced pressure
  3. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-6e072d5c34b1454b821bf4b756b1b6b1
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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