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

HRID 1250898

반응식

HRID 1250898 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-87b31028294e4602931608be0f5cbc66
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06340687B1

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