Ammonia → 4-(5-Phenyl-1,3,4-oxadiazol-2-yl)piperidine

HRID 713411Notes

Reaction equation

HRID 713411 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:17][N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.N>C(Cl)Cl.CO>[C:19]1([C:16]2[O:15][C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:18][N:17]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 21098365Tert-butyl 4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 27611504-(5-Phenyl-1,3,4-oxadiazol-2-yl)piperidineYield 100.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (795 mg, 2.41 mmol, 1.0 eq) in CH2Cl2 was added TFA (1.5 mL, 19.5 mmol, 8 eq). The reaction was stirred for 1 h and 7 N NH3 in MeOH (2 mL) was added dropwise for the pH to reach 7. The solvent was evaporated in vacuo giving the title product as a white solid (553 mg) which was used without further purification for the next step. MS (m/z, MH+): 230.3

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-548b14000e75434788e6d266527434ca
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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