Butanal → HCID 44181559, compound

HRID 415349Notes

Reaction equation

HRID 415349 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][CH2:31]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][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 261ButanalHCID 66621374HCID 66621374, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44181559HCID 44181559, compoundYield 13.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (400 mg, 1.06 mmol), Pd/C (10% wt, 40 mg), butyraldehyde (96 mg, 1.58 mmol) in anhydrous methanol (15 mL) was purged with hydrogen at room temperature for 12 hr. The mixture was filtered and the filtrate was concentrated to give crude product. The crude product was purified by prep-HPLC to give 2-(1-butylpiperidin-4-yl)benzo[d]oxazol-7-carboxamide (44 mg, yield 13%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 0.94 (t, 3H), 1.30-1.48 (m, 2H), 1.48-1.55 (m, 2H), 2.03-2.11 (m, 6H), 2.36-2.41 (m, 2H), 3.00-3.06 (m, 3H), 6.20 (s, 1H); 6.99 (s, 1H), 7.42-7.46 (t, 1H), 7.85-7.87 (m, 1H), 8.07 (dd, 1H); LC-MS (ESI) m/z: 302 (M+1)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give crude product
  4. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-4df711b66ffd4933b0c0725637795487
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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