Hydrochloric Acid → HCID 67242508, compound

HRID 2421983Notes

Reaction equation

HRID 2421983 reaction equation
[F: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.CO.[ClH:29]>O1CCOCC1>[ClH:29].[ClH:29].[F: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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 86625875HCID 86625875, compound

Product 1

HCID 67242508HCID 67242508, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (1-(5-fluoropyridin-2-yl)piperidin-4-yl)carbamate (0.36 g, 1.22 mmol) in HCl in Dioxane (4M, 2 mL), THF (2 mL) and MeOH (2 mL) was stirred at rt. After 4 h the reaction mixture was filtered, the residue washed with EtOAc and dried to give the title compound (0.31 g, 96%) as a solid. 1H NMR (500 MHz, CD3OD): 8.10-8.02 (m, 2H), 7.52 (dd, 1H), 4.34-4.26 (m, 2H), 3.61-3.50 (m, 1H), 3.38 (dt, 2H), 2.28-2.21 (m, 2H), 1.80 (dq, 2H); 13C NMR (CD3OD): 153.2, 151.2, 151.0, 134.5, 134.3, 123.9, 123.6, 115.0, 114.9, 45.3, 29.1; Mass Spectrum: M+H 196.

Workup

  1. filtrationAfter 4 h the reaction mixture was filtered
  2. washthe residue washed with EtOAc
  3. customdried

Sources & evidence

ORD record
ord-4bc35e602aab497bbbcb6ff8b3062d6c
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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