Trifluoroacetic acid → 4-Amino-1-(5-piperid-1-ylcarbonyl-2-pyridyl)piperidine

HRID 23565Notes

Reaction equation

HRID 23565 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[O:22])=[CH:17][N:16]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 225744534-Tert-butoxycarbonylamino-1-(5-piperid-1-ylcarbonyl-2-pyridyl)piperidine

Product 1

HCID 113007004-Amino-1-(5-piperid-1-ylcarbonyl-2-pyridyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.475 g of 4-tert-butoxycarbonylamino-1-(5-piperid-1-ylcarbonyl-2-pyridyl)piperidine (1.24 mmol) and 5 ml of trifluoroacetic acid in 20 ml of dichloromethane is stirred for 1 hour. The reaction medium is concentrated under reduced pressure and then taken up in dichloromethane. The solution is basified (pH=9) using saturated aqueous sodium carbonate solution. The aqueous phase is extracted five times with dichloromethane. The organic phases are dried over magnesium sulfate and concentrated under reduced ressure. The 4-amino-1-(5-piperid-1-ylcarbonyl-2-pyridyl)piperidine is obtained in the form of an oil (0.310 g, 88%). [M+H+]=289.4

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. extractionThe aqueous phase is extracted five times with dichloromethane
  3. dry with materialThe organic phases are dried over magnesium sulfate
  4. concentrationconcentrated under reduced ressure

Sources & evidence

ORD record
ord-a2f089456b464a99be748955170ba9f6
Source dataset
uspto-grants-2005_02
Patent number
US06852736B2

Reaction notes

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