Tetrahydrofuran → HCID 67242138, compound

HRID 2239581Notes

Reaction equation

HRID 2239581 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C1COCC1>Cl.O1CCOCC1>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86625876HCID 86625876, compound

Product 1

HCID 67242138HCID 67242138, compoundYield 302%

Reagents, catalysts & solvents 2

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

Procedure

A solution of tert-butyl (1-(5-chloropyridin-2-yl)piperidin-4-yl)carbamate (1.15 g, 3.70 mmol) in HCl in Dioxane (4M, 5 mL) and THF (5 mL) was stirred at rt for 6.5 h. 4M HCl in Dioxane (2 mL) was added and the reaction mixture stirred for another 20 h. The reaction mixture was filtered, the residue was washed with EtOAc and dried to give the title compound (1.06 g, 100%) as a solid. 1H NMR (500 MHz, CD3OD): 8.10 (s, 1H), 8.06 (d, 1H), 7.52 (d, 1H), 4.36 (d, 2H), 3.62-3.54 (m, 1H), 3.42 (dt, 2H), 2.18 (d, 2H), 1.82 (dq, 2H); 13C NMR (CD3OD): 151.4, 144.4, 134.6, 120.0, 114.7, 45.2, 29.1; Mass Spectrum: M+H 212.

Workup

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

Sources & evidence

ORD record
ord-0fd280e462ff4a87b813dc90ee0f7572
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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