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

HRID 2230

반응식

HRID 2230 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 31260Isoamyl Alcohol용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a48b81fc6740494aa3b8c87fee1bf7d7
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728701

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