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

HRID 415267Notes

Reaction equation

HRID 415267 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 25.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (100 mg, 0.26 mmol), 10% Pd/C (20 mg) in methanol (30 mL) was stirred at room temperature over 1 atm hydrogen for 2 hr. The mixture was evaporated under reduced pressure and purified by pre-HPLC to give 16 mg of 2-(piperidin-3-yl)benzo[d]oxazole-7-carboxamide as a solid. Yield 25%. 1H-NMR (400 MHz, DMSO-d6): δ 1.50-1.53 (m, 1H), 1.65-1.67 (m, 1H), 1.81-1.84 (m, 1H), 2.16-2.19 (m, 1H), 2.50-2.54 (m, 1H), 2.81-2.90 (m, 2H), 3.07-3.12 (m, 1H), 3.28-3.31 (m, 1H), 7.39-7.43 (t, J=8.0 Hz, 1H), 7.72-7.78 (m, 3H), 7.83-7.85 (m, 1H). LC-MS (ESI) m/z: 246 (M+1)+.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. custompurified by pre-HPLC

Sources & evidence

ORD record
ord-cc80d01a8cb543a4bc105a3c18ad2586
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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