Trifluoroacetic acid → 1-[(Pyridin-3-yl)methyl]piperazine

HRID 912382Notes

Reaction equation

HRID 912382 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=O)(C)(C)C.Cl.ClC[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(O)(C(F)(F)F)=O>CN(C=O)C>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH2:6][N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[CH:18]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 1569751-[(Pyridin-3-yl)methyl]piperazineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperazine-1-carboxylic acid tert-butyl ester (930 mg), 3-chloromethyl-pyridine hydrochloride (902 mg) and cesium carbonate (3.6 g) were reacted in DMF (5 ml), followed by further treatment with TFA, to obtain 1-pyridin-3-ylmethyl-piperazine (767 mg, 87%) as a pale brown oil.

Sources & evidence

ORD record
ord-f3c59fc866cb44d59b6f6f687329f2d8
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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