Triethylamine → N-(3-hydroxy-6-methoxy-2,4,5-trimethylbenzyl)-N-methyl-2-(4-acetyl-2-isopropyl-5-methylphenoxy)ethylamine

HRID 55386노트

반응식

HRID 55386 반응식
[CH3:1][NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13](=[O:15])[CH3:14])=[CH:8][C:7]=1[CH:16]([CH3:18])[CH3:17].[OH:19][C:20]1[C:21]([CH3:32])=[C:22]([C:25]([O:30][CH3:31])=[C:26]([CH3:29])[C:27]=1[CH3:28])[CH2:23]Cl.C(N(CC)CC)C>CN(C)C=O>[OH:19][C:20]1[C:21]([CH3:32])=[C:22]([C:25]([O:30][CH3:31])=[C:26]([CH3:29])[C:27]=1[CH3:28])[CH2:23][N:2]([CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13](=[O:15])[CH3:14])=[CH:8][C:7]=1[CH:16]([CH3:18])[CH3:17])[CH3:1]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 109218743-Hydroxy-6-methoxy-2,4,5-trimethylbenzyl chlorideHCID 19957706N-Methyl-2-(4-acetyl-2-isopropyl-5-methylphenoxy)ethylamine

생성물 1

HCID 19957713N-(3-hydroxy-6-methoxy-2,4,5-trimethylbenzyl)-N-methyl-2-(4-acetyl-2-isopropyl-5-methylphenoxy)ethylamine수율 95.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-Methyl-2-(4-acetyl-2-isopropyl-5-methylphenoxy)ethylamine (6.75 g) and 3-hydroxy-6-methoxy-2,4,5-trimethylbenzyl chloride (5.48 g) were dissolved in N,N-dimethylformamide (80 ml), and triethylamine (2.58 g) was added dropwise while stirring the mixture at room temperature. The mixture was stirred at room temperature for 16.5 hours. After the reaction, the solvent was distilled off, and water was added. The mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained liquid was purified by silica gel chromatography (eluent; ethyl acetate/benzene=1/1) to give 10.38 g of a pale-yellow solid. The obtained solid was recrystallized from isopropyl alcohol to give 7.22 g of the title compound (colorless crystals).

후처리

  1. stirringThe mixture was stirred at room temperature for 16.5 hours
  2. customAfter the reaction
  3. distillationthe solvent was distilled off
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe obtained organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe obtained liquid was purified by silica gel chromatography (eluent; ethyl acetate/benzene=1/1)

출처 및 근거

ORD 기록
ord-c77fd0935e2f4c4cbcf3ad0c6303cb8c
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624961

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