Hydrochloric Acid → 1-(Pyridin-2-yl)piperidin-4-amine dihydrochloride

HRID 2239579Notes

Reaction equation

HRID 2239579 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][CH:10]([NH:13]C(=O)OC(C)(C)C)[CH2:9][CH2:8]1.C1COCC1.CO.[ClH:28]>O1CCOCC1>[ClH:28].[ClH:28].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][CH:10]([NH2:13])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 537924442-(4-Boc-Aminopiperidino)pyridine

Product 1

HCID 666310961-(Pyridin-2-yl)piperidin-4-amine dihydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (1-pyridin-2-ylpiperidin-4-yl)carbamate (0.64 g, 2.31 mmol) in HCl in Dioxane (4M, 3.5 ml), THF (2.5 ml) and MeOH (2 ml) was stirred at rt for 17 h. The reaction mixture was filtered, the residue washed with EtOAc and dried to give the title compound (0.49 mg, 85%) as a solid. 1H NMR (500 MHz, D2O): 7.91 (dd, 1H), 7.78 (d, 1H), 7.22 (d, 1H), 6.88 (t, 1H), 4.12 (d, 2H), 3.56-3.48 (m, 1H), 3.26 (t, 2H), 2.15 (d, 2H), 1.67 (dq, 2H); 13C NMR (D2O): 152.1, 144.7, 135.9, 113.3, 47.6, 44.7, 28.8; Mass Spectrum: M+H 178

Workup

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

Sources & evidence

ORD record
ord-5634d6d40da64004b296b330adc1258b
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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