Ammonia → Benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate

HRID 415308Notes

Reaction equation

HRID 415308 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[O:18][C:19]3[C:25]([C:26](OC)=[O:27])=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:30]>CO>[C:26]([C:25]1[C:19]2[O:18][C:17]([CH:13]3[CH2:14][CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:10])[CH2:12]3)=[N:21][C:20]=2[CH:22]=[CH:23][CH:24]=1)(=[O:27])[NH2:30]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66620844Methyl 2-(1-(benzyloxycarbonyl)piperidin-3-yl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 66621433Benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylateYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(1-(benzyloxycarbonyl)piperidin-3-yl)benzo[d]oxazole-7-carboxylate (360 mg, 0.92 mmol) was added to a solution of ammonia in methanol (10 mL) and the mixture was stirred at room temperature overnight. Then the mixture was evaporated under reduced pressure and extracted with ethyl acetate (100 mL×4), the organic phase was dried with anhydrous sodium sulfate and evaporated under reduced pressure. 200 mg benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate was obtained. Yield: 26%. LC-MS (ESI) m/z: 380 (M+1)+.

Workup

  1. customThen the mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (100 mL×4)
  3. dry with materialthe organic phase was dried with anhydrous sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-da0d6d833b11436f8d378319cccda2e1
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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