Toluene → N-[2-(4-chlorobenzyloxy)-1,1-dimethylethyl]-3-(imidazol-1-yl)propylamine

HRID 2268253노트

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HRID 2268253 반응식
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.C1(C)C=CC=CC=1>CC(N(C)C)=O>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:12][CH2:11][C:10]([NH:9][CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)([CH3:14])[CH3:13])=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 183497652-[3-(Imidazol-1-yl)propylamino]-2-methyl-1-propanol

생성물 1

HCID 18349726N-[2-(4-chlorobenzyloxy)-1,1-dimethylethyl]-3-(imidazol-1-yl)propylamine

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매3회

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온도
30 °C

실험 절차

A solution of 2-[3-(imidazol-1-yl)propylamino]-2-methyl-1-propanol (1.5 g) in dimethyl acetamide (10 ml) was added dropwise to a stirred suspension of sodium hydride (0.32 g of a 60% dispersion in mineral oil) in dimethyl acetamide (15 ml) at 30° C. under nitrogen. The mixture was stirred for 45 minutes at 30° C. and then a solution of 4-chlorobenzyl chloride (1.63 g) in dimethyl acetamide (5 ml) was added. After the addition, the mixture was heated at 100-105° C. for 30 minutes and then cooled to 25° C. Toluene (50 ml) was added and the mixture was washed with water. The toluene layer was extracted with 5M hydrochloric acid. The combined acid extracts were basified with concentrated sodium hydroxide solution with cooling and extracted with dichloromethane to give an oil which was distilled under high vacuum to give N-[2-(4-chlorobenzyloxy)-1,1-dimethylethyl]-3-(imidazol-1-yl)propylamine, b.p. 180-185° C. at 0.3 mbar.

후처리

  1. additionAfter the addition
  2. temperaturethe mixture was heated at 100-105° C. for 30 minutes
  3. temperaturecooled to 25° C
  4. washthe mixture was washed with water
  5. extractionThe toluene layer was extracted with 5M hydrochloric acid
  6. temperaturewith cooling
  7. extractionextracted with dichloromethane
  8. customto give an oil which
  9. distillationwas distilled under high vacuum

출처 및 근거

ORD 기록
ord-4a0ff415b89949c7861f7f36b99955e0
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326500B1

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