Methanol → HCID 86625874, compound

HRID 2421980Notes

Reaction equation

HRID 2421980 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1COCC1.CO>Cl.O1CCOCC1>[ClH:1].[ClH:1].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 53486065HCID 53486065, compound

Product 1

HCID 86625874HCID 86625874, compoundYield 277.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl [1-(6-chloropyridin-3-yl)-piperidin-4-yl)carbamate (1.211 g, 3.88 mmol) in HCl in Dioxane (4M, 5 mL), THF (5 mL) and MeOH (4 mL) was stirred at rt for 20 h. The reaction mixture was filtered, the residue washed with EtOAc and dried to give the title compound (1.02 g, 92%) as a solid; 1H NMR (500 MHz, CD3OD): 8.36 (d, 1H), 7.97 (dd, 1H), 7.68 (d, 1H), 4.05-3.96 (m, 2H), 3.51-3.41 (m, 1H), 3.18 (dt, 2H), 2.24-2.17 (m, 2H), 1.85 (dq, 2H); 13C NMR (CD3OD): 145.8, 136.7, 133.3, 130.7, 126.5, 47.1, 28.9; Mass Spectrum: M+H 212.

Workup

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

Sources & evidence

ORD record
ord-9f2b4e4020e842ca9d524fb52d6a1b49
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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