Potassium Iodide → 4-(4-Methylsulfonylaminobenzoyl)-1-[2-(3-pyridyl)ethyl]piperidine dihydrochloride

HRID 982358ノート

反応式

HRID 982358 の反応式
[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl.[Cl:28][CH2:29][CH2:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1.[I-].[K+]>CN(C)C=O>[ClH:28].[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][N:16]([CH2:29][CH2:30][C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH2:15][CH2:14]2)=[O:12])=[CH:19][CH:20]=1)(=[O:4])=[O:5]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 199465Pyridine, 3-(2-chloroethyl)-, hydrochlorideHCID 14130042N-[4-(piperidine-4-carbonyl)-phenyl]methanesulfonamide hydrochloride

生成物 1

HCID 141300464-(4-Methylsulfonylaminobenzoyl)-1-[2-(3-pyridyl)ethyl]piperidine dihydrochloride収率 28.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

35 g (0.101 mol) of 4-(4-methylsulfonylaminobenzoyl)piperidine hydrochloride and 55 g of potassium carbonate were suspended in 700 ml of dimethylformamide and the suspension was stirred at 40° C. for 20 min. 19.6 g (0.101 mol) of 3-(2-chloroethyl)pyridine hydrochloride and 6.0 g (0.036 mol) of potassium iodide were added to the suspension and the mixture was stirred at 90° C. for 3.5 h. The liquid reaction mixture was filtered and the filtrate was concentrated, while the residue was purified according to silica gel chromatography (chloroform:methanol=93:7). The purified product was converted into its hydrochloride with ethanolic hydrogen chloride and recrystallized from methanol/isopropanol to obtain 13.4 g of the intended compound.

後処理

  1. stirringthe mixture was stirred at 90° C. for 3.5 h
  2. customThe liquid reaction mixture
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated, while the residue
  5. customwas purified
  6. customrecrystallized from methanol/isopropanol

出典と根拠

ORDレコード
ord-45fa37e1bbff4bbba6c3b088319bb08f
出典データセット
uspto-grants-1991_02
特許番号
US04996215

反応ノート

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