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

HRID 415266Notes

Reaction equation

HRID 415266 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 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(1-(benzyloxycarbonyl)piperidin-3-yl)benzo[d]oxazole-7-carboxylate (180 mg, 0.46 mmol) was added to ammonia in methanol (20 mL) and the mixture was stirred at room temperature for 2 days. 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. 100 mg of benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate was obtained. Yield: 57%. 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-ced4f67fbb554dafbb78403e103be6f0
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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