Sodium Iodide → N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine

HRID 447749노트

반응식

HRID 447749 반응식
Cl[CH2:2][CH2:3][CH:4]1[CH2:12][CH2:11][CH2:10][C:9]2[N:8]([CH3:13])[CH:7]=[CH:6][C:5]1=2.[CH3:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[CH2:16]([N:15]([CH3:14])[CH2:2][CH2:3][CH:4]1[CH2:12][CH2:11][CH2:10][C:9]2[N:8]([CH3:13])[CH:7]=[CH:6][C:5]1=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 690791294-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole

생성물 1

HCID 17751624N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine수율 28%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole (0.1 g, 0.5 mmol), N-methyl-N-benzylamine (0.07 g, 0.5 mmol), K2CO3 (0.20 g, 1.45 mmol) and a catalytic amount of NaI in DMF (5 mL) is heated to 110° C. overnight. The solvent is removed at reduced pressure, diethyl ether is added to the residue and washed with water. The organic phase is dried and evaporated at reduced pressure and the resulting crude is purified by column chromatography, giving N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine (0.04 g, 0.14 mmol, 28%, oil). (ESI-MS m/z 283 (M+H)+.

후처리

  1. customThe solvent is removed at reduced pressure, diethyl ether
  2. additionis added to the residue
  3. washwashed with water
  4. customThe organic phase is dried
  5. customevaporated at reduced pressure
  6. customthe resulting crude is purified by column chromatography

출처 및 근거

ORD 기록
ord-cb149c94882848bd882c1aa86324c406
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481567B2

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