Tetrahydrofuran → HCID 67242138, compound

HRID 2421984Notes

Reaction equation

HRID 2421984 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-12c8e2fa6053443a81bd47cb122a9363
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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