Sodium Bicarbonate → 4-Acetylamino-1-(4-pyridyl)piperidine

HRID 743833

Reaction equation

HRID 743833 reaction equation
Cl.[C:2]([NH:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:4])[CH3:3].Cl.Cl[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])O.[Na+]>CC(C)CCO>[C:2]([NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:18]2[CH:17]=[CH:16][N:15]=[CH:14][CH:19]=2)[CH2:8][CH2:7]1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 114011054-Acetamidopiperidine dihydrochlorideHCID 156199202-Chloropyridine--hydrogen chloride (1/1)

Product 1

HCID 189184354-Acetylamino-1-(4-pyridyl)piperidine

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of the product from step (ii) (1.79 g), -chloropyridine hydrochloride (1.50 g), sodium hydrogen carbonate (2.86 g) in 3-methyl 1-butanol (25 ml) was heated at reflux temperature for 16 hours. The cooled mixture was filtered and the filtrate concentrated in vacuo. Purification of the residue by flash chromatography on silica, eluting with methanol/dichloromethane (1:2 v/v) gave 4-acetylamino-1-(4-pyridyl)piperidine as a foam, 0.69 g: NMR(d6DMSO) δ8.10(2H,d), 7.80(1H,bd), 6.80(2H,dd), 3.82(3H,m), 2.93(2H,dt), 1.78(3H,s), 1.77(2H,m), 1.33(2H,dq); m/e 220 (M+H)+.

Workup

  1. temperatureat reflux temperature for 16 hours
  2. filtrationThe cooled mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica
  5. washeluting with methanol/dichloromethane (1:2 v/v)

Sources & evidence

ORD record
ord-ba47285be3294e308a6711f86a149141
Source dataset
uspto-grants-1996_09
Patent number
US05556977

Linked notes

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