4-Chloropyridine hydrochloride → 4-Acetylamino-1-(4-pyridyl)piperidine

HRID 1291877Notes

Reaction equation

HRID 1291877 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][N:17]=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>CC(C)CCO>[C:2]([NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 818524-Chloropyridine hydrochlorideHCID 516892Sodium BicarbonateHCID 114011054-Acetamidopiperidine dihydrochloride

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), 4-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) δ 8.10(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. temperaturewas heated
  2. temperatureat reflux temperature for 16 hours
  3. filtrationThe cooled mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customPurification of the residue by flash chromatography on silica
  6. washeluting with methanol/dichloromethane (1:2 v/v)

Sources & evidence

ORD record
ord-edf5695b9fd94b3e8617eba00e2e6053
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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