Tetrahydrofuran → HCID 65815895, compound

HRID 2239583Notes

Reaction equation

HRID 2239583 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH2:10]2)[CH:4]=1.C1COCC1>Cl.O1CCOCC1>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]2)[CH:4]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86625877Tert-butyl {1-[4-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)carbamate

Product 1

HCID 65815895HCID 65815895, compoundYield 130.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl {1-[4-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)carbamate (1.07 g, 3.09 mmol) in HCl in Dioxane (4M, 5 mL) and THF (5 mL) was stirred at rt for 6.5 h. HCl in Dioxane (4M, 2 mL) was added and the reaction mixture was stirred for another 20 h. The reaction mixture was filtered, the residue washed with EtOAc and dried to give the title compound (0.99 g, 100%) as a solid. 1H NMR (500 MHz, CD3OD): 8.19 (d, 1H), 7.82 (s, 1H), 7.22 (d, 1H), 4.64 (d, 2H), 3.66-3.56 (m, 1H), 3.52 (td, 2H), 3.29 (d, 2H), 1.87 (dq, 2H); 13C NMR (CD3OD): 152.6, 144.8, 144.5, 144.2, 143.9, 138.7, 125.3, 123.1, 120.9, 118.7, 111.2, 108.1, 45.3, 29.0; Mass Spectrum: M+H 246

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue washed with EtOAc
  3. customdried

Sources & evidence

ORD record
ord-ee13cf37d1e84844bee460bdcaa82d09
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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