Propanal → HCID 44181557, compound

HRID 415350Notes

Reaction equation

HRID 415350 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([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)[CH2:2]1.[CH:25](=O)[CH2:26][CH3:27].[BH4-].[Na+]>CO>[CH2:25]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([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)[CH2:2]1)[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 527PropanalHCID 4311764Sodium borohydrideHCID 44181679HCID 44181679, compound

Product 1

HCID 44181557HCID 44181557, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(4-(piperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide (80 mg, 0.25 mmol) and propionaldehyde (72 mg, 1.25 mmol) in methanol (10 mL) was stirred at room temperature for 40 min. Then the mixture was cooled to 0° C. Sodium borohydride (45 mg, 0.75 mmol) was added. After the addition, the mixture was stirred at this temperature for 2 hr. Methanol was removed under reduced pressure. The residue was washed with ethyl acetate/methanol (10/1) and filtered. The filtrate was concentrated to give the crude product. The crude product was purified by pre-HPLC to give 2-(4-(1-propylpiperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide as a light yellow solid (18 mg, yield 23%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 0.94 (t, 3H), 1.58-1.64 (m, 3H), 1.81-2.01 (m, 3H), 2.11-2.20 (m, 2H), 2.43 (m, 2H), 2.97 (m, 1H), 3.08 (t, 2H), 7.50-7.54 (m, 3H), 7.91-7.94 (m, 2H), 8.29 (d, 1H); LC-MS (ESI) m/z: 364 (M+1)+.

Workup

  1. temperatureThen the mixture was cooled to 0° C
  2. additionAfter the addition
  3. stirringthe mixture was stirred at this temperature for 2 hr
  4. customMethanol was removed under reduced pressure
  5. washThe residue was washed with ethyl acetate/methanol (10/1)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto give the crude product
  9. customThe crude product was purified by pre-HPLC

Sources & evidence

ORD record
ord-2dac62cf950a4266b7c07a7079f3da31
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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