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

HRID 447749ノート

反応式

HRID 447749 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-cb149c94882848bd882c1aa86324c406
出典データセット
uspto-grants-2013_07
特許番号
US08481567B2

反応ノート

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