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

HRID 1006059

반응식

HRID 1006059 반응식
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

참가 물질

8

반응물 6

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-42d154bb417940aa99b4d83fad8fa025
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787560B2

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