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Triethylamine → Tert-butyl 2-(3-(3-cyanophenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate

HRID 1791360
Notes
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Reaction equation

HRID 1791360 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[C:32]([C:34]1[CH:35]=[C:36]([CH:41]=[CH:42][CH:43]=1)[C:37]([NH:39]O)=[NH:38])#[N:33]>C1COCC1.ClCCl.O.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[O:16][N:39]=[C:37]([C:36]2[CH:41]=[CH:42][CH:43]=[C:34]([C:32]#[N:33])[CH:35]=2)[N:38]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 5818311-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 178509779HCID 178509779, compound

Product 1

HCID 69619392Tert-butyl 2-(3-(3-cyanophenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylateYield 98.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (5.32 g, 23.2 mmol) and triethylamine (4.04 g, 40 mmol) in THF (50 mL), isobutyl chloroformate (3.0 mL, 25.5 mmol) was added dropwise. After the mixture was stirred at room temperature for 45 min, 3-cyano-N-hydroxy-benzamidine (3.7 g, 23.2 mmol) and DMF (40 mL) were added. After being stirred for another hour, the reaction mixture was heated to 130˜135° C. for 1.5 h. Then the solution was cooled to room temperature and poured into water. Dichloromethane was used to extract the product. The organic layer was dried with sodium sulfate and concentrated in vacuo to give 8.1 g (98.4%) of the title compound as a thick brown oil.

Workup

  1. additionwas added dropwise
  2. stirringAfter being stirred for another hour
  3. temperaturethe reaction mixture was heated to 130˜135° C. for 1.5 h
  4. temperatureThen the solution was cooled to room temperature
  5. extractionto extract the product
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f98dd5e94fc24360a3b4c09c127afdb6
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074809B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes