Hydrochloric Acid → 1-[5-(Trifluoromethyl)pyridin-2-yl]piperidin-4-amine dihydrochloride

HRID 2239593Notes

Reaction equation

HRID 2239593 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH2:10]2)=[N:7][CH:8]=1.[ClH:25]>O1CCOCC1.C1COCC1.O1CCOCC1>[ClH:25].[ClH:25].[F:24][C:2]([F:1])([F:23])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]2)=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86625881Tert-butyl {1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}carbamate

Product 1

HCID 672434721-[5-(Trifluoromethyl)pyridin-2-yl]piperidin-4-amine dihydrochlorideYield 89%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 22018518Dioxane tetrahydrofuranSolvent

Procedure

A mixture of tert-butyl {1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}carbamate (1.27 g, 3.68 mmol) in HCl in Dioxane/THF (4M, 1:1; 10 ml) was stirred at rt. After 6.5 h more HCl in Dioxane (4M, 2 ml) was added and the resulting mixture stirred for a further 18 h. The mixture was filtered and the residue was washed with EtOAc to give the title compound (1.04 g, 89%) as a solid. 1H NMR (500 MHz CD3OD): 8.35 (s, 1H), 8.20 (dd, 1H), 7.60 (d, 1H), 4.46 (d, 2H), 3.66-3.56 (m, 1H), 3.48 (td, 2H), 2.28 (d, 2H), 1.90-1.80 (m, 2H); 13C NMR (125 MHz CD3OD): 153.5, 139.2, 136.3, 126.1, 123.9, 121.8, 120.0, 116.2, 115.9, 115.6, 115.3, 113.9, 45.2, 29.1; Mass Spectrum: M+H+ 246.

Workup

  1. stirringthe resulting mixture stirred for a further 18 h
  2. filtrationThe mixture was filtered
  3. washthe residue was washed with EtOAc

Sources & evidence

ORD record
ord-e811fe7c6d2f4e88a11bd57ca52a83f4
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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