Trifluoroacetic acid → 3-(Piperidin-4-ylmethyl)pyridine

HRID 862737Notes

Reaction equation

HRID 862737 reaction equation
CC(C)(OC([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:9][CH2:8]1)=O)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH2:13][CH:10]2[CH2:11][CH2:12][NH:7][CH2:8][CH2:9]2)[CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 185388801-(1,1-Dimethylethyloxycarbonyl)-4-(3-pyridylmethyl)piperidine

Product 1

HCID 37932203-(Piperidin-4-ylmethyl)pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-(1,1-dimethylethyloxycarbonyl)-4-(3-pyridylmethyl)piperidine (500 mg, 1.80 mmol) in chloroform (14 mL) was cooled to 0° C. and treated with trifluoroacetic acid (5 mL, 65.14 mmol). The resulting mixture was stirred for 1 h and then made basic by addition of aqueous sodium hydroxide. The organic extracts were separated and the aqueous was reextracted three more times with chloroform. The chloroform extracts were combined, dried over sodium sulfate, filtered and concentrated on a rotary evaporator to give the title compound as a colorless oil (300 mg, 1.70 mmol, 95%).

Workup

  1. customThe organic extracts were separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-fb6be0b8edce460b8568a5637de71777
Source dataset
uspto-grants-1998_02
Patent number
US05719166

Reaction notes

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