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

HRID 864838

反応式

HRID 864838 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31260Isoamyl Alcohol溶媒

実験手順

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) 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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-7ba60f015b3145719f7c251087acb0b5
出典データセット
uspto-grants-1996_10
特許番号
US05563141

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