Ethylamine → N'-(6-Chloro-2-methyl-phenyl)-N-ethyl-propane-1,3-diamine

HRID 1250898

反応式

HRID 1250898 の反応式
[CH2:1]([NH2:3])[CH3:2].[Cl:4][C:5]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14]O)=[C:9]([CH3:16])[CH:8]=[CH:7][CH:6]=1>O1CCCC1.ClCCl>[Cl:4][C:5]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14][NH:3][CH2:1][CH3:2])=[C:9]([CH3:16])[CH:8]=[CH:7][CH:6]=1

参加物

5

反応物 2

HCID 6341EthylamineHCID 183248341-(6-Chloro-2-methyl-phenyl)amino-3-hydroxy-propane

生成物 1

HCID 18324822N'-(6-Chloro-2-methyl-phenyl)-N-ethyl-propane-1,3-diamine収率 54.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of a 2.0 M solution of ethylamine in tetrahydrofuran (139.5 mL) and the hydrobromide salt of Example 12, Step A (9.5 g) was stirred at ambient temperature under nitrogen for 48 hours. The tetrahydrofuran was removed in vacuo and the residue was partitioned between dichloromethane and 1N sodium hydroxide. The extracts were washed with brine, dried over sodium sulfate, and concentrated in vacuo to give a brown oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with a solvent gradient (from 95:5 to 80:20 dichloromethane-methanol containing 0.2% ammonium hydroxide) gave the title compound (3.4 g, 54.3%) as a yellow oil, which was used as such in the next step.

後処理

  1. customThe tetrahydrofuran was removed in vacuo
  2. customthe residue was partitioned between dichloromethane and 1N sodium hydroxide
  3. washThe extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. customabsorbed onto a column of Merck-60 flash silica gel
  8. washElution with a solvent gradient (from 95:5 to 80:20 dichloromethane-methanol containing 0.2% ammonium hydroxide)

出典と根拠

ORDレコード
ord-87b31028294e4602931608be0f5cbc66
出典データセット
uspto-grants-2002_01
特許番号
US06340687B1

関連ノート

読み込み中…