Benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate → 2-(Piperidin-3-yl)benzo[d]oxazole-7-carboxamide

HRID 415309Notes

Reaction equation

HRID 415309 reaction equation
[C:1]([C:4]1[C:12]2[O:11][C:10]([CH:13]3[CH2:18][CH2:17][CH2:16][N:15](C(OCC4C=CC=CC=4)=O)[CH2:14]3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[H][H]>CO.[Pd]>[NH:15]1[CH2:16][CH2:17][CH2:18][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)[CH2:14]1

Participants

5

Reactant 2

HCID 66621433Benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 666209242-(Piperidin-3-yl)benzo[d]oxazole-7-carboxamideYield 241.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (200 mg, 0.27 mmol), 10% Pd/C (40 mg) in methanol (30 ml) was stirred at room temperature over 1 atm hydrogen for 2 hr. Then the mixture was filtered and evaporated, 160 mg of 2-(piperidin-3-yl)benzo[d]oxazole-7-carboxamide as a solid was obtained. Yield 24%. LC-MS (ESI) m/z: 246 (M+1)+.

Workup

  1. filtrationThen the mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-320e711268134a44bbb970d558ba9474
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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