Trifluoroacetic acid → (RS)-2-(5-Phenyl-[1,3,4]oxadiazol-2-ylmethyl)-piperidine

HRID 549318

Reaction equation

HRID 549318 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][N:19]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:20]1([C:17]2[O:16][C:15]([CH2:14][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[N:19][N:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 86628996(RS)-2-(5-Phenyl-[1,3,4]oxadiazol-2-ylmethyl)-piperidine-1-carboxylic acid tert butyl ester

Product 1

HCID 67157689(RS)-2-(5-Phenyl-[1,3,4]oxadiazol-2-ylmethyl)-piperidineYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (RS)-2-(5-phenyl-[1,3,4]oxadiazol-2-ylmethyl)-piperidine-1-carboxylic acid tert butyl ester (0.175 g) in dichloromethane (4 ml) was cooled (ice bath) and treated with trifluoroacetic acid (1 ml). The mixture was stirred for 1 h, added to saturated potassium carbonate and the product extracted into dichloromethane. The organic phase was dried (MgSO4) and solvent removed at reduced pressure to give the title compound (0.115 g)

Workup

  1. extractionthe product extracted into dichloromethane
  2. dry with materialThe organic phase was dried (MgSO4) and solvent
  3. customremoved at reduced pressure

Sources & evidence

ORD record
ord-87e2773e6e7042bfb799c4cc0a702471
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Linked notes

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