Potassium Iodide → N-(2-(1-naphthyl)ethyl)-4-(2-bromo-5-methoxybenzyl)piperidine

HRID 1006059

反応式

HRID 1006059 の反応式
CS(Cl)(=O)=O.[C:6]1([CH:16](O)[CH3:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.Cl.[Br:27][C:28]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:29]=1[CH2:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:6]1([CH2:16][CH2:17][N:34]2[CH2:33][CH2:32][CH:31]([CH2:30][C:29]3[CH:37]=[C:38]([O:41][CH3:42])[CH:39]=[CH:40][C:28]=3[Br:27])[CH2:36][CH2:35]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

参加物

8

反応物 6

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 980301-(1-Naphthyl)ethanolHCID 226753344-(2-Bromo-5-methoxybenzyl)piperidine hydrochloride

生成物 1

HCID 12968873N-(2-(1-naphthyl)ethyl)-4-(2-bromo-5-methoxybenzyl)piperidine収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methanesulfonyl chloride (100 μl, 1.26 mmol) was added dropwise to a solution of 1-naphthylethanol (206 mg, 1.20 mmol) and triethylamine (350 μl, 2.40 mmol) in dichloromethane (2 ml) under ice-cooling and stirred for 3 hours. The solvent was distilled off and the resulting residue was dissolved in acetonitrile (3 ml) together with a base converted from 4-(2-bromo-5-methoxybenzyl)piperidine hydrochloride (384 mg, 1.20 mmol) according to the method described in Example 11, potassium iodide (199 mg, 1.20 mmol) and potassium carbonate (332 mg, 2.40 mmol). The resulting solution was heated under reflux for 3.5 hours and then allowed to cool. The precipitate was filtered off and the filtrate was concentrated, and then the residue was purified by a silica gel column chromatography (chloroform:methanol=20:1) to obtain the title compound (425 mg, 81%) as a light-brown solid.

後処理

  1. temperaturecooling
  2. distillationThe solvent was distilled off
  3. dissolutionthe resulting residue was dissolved in acetonitrile (3 ml) together with a base
  4. temperatureThe resulting solution was heated
  5. temperatureunder reflux for 3.5 hours
  6. temperatureto cool
  7. filtrationThe precipitate was filtered off
  8. concentrationthe filtrate was concentrated
  9. customthe residue was purified by a silica gel column chromatography (chloroform:methanol=20:1)

出典と根拠

ORDレコード
ord-42d154bb417940aa99b4d83fad8fa025
出典データセット
uspto-grants-2004_09
特許番号
US06787560B2

関連ノート

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