Hydrochloric Acid → HCID 18933629, 화합물

HRID 1598302노트

반응식

HRID 1598302 반응식
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])[CH3:3].[H-].[Na+].[Cl:14][CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19].[ClH:22].[OH-].[Na+]>CN(C=O)C.C1(C)C=CC=CC=1.O>[ClH:14].[ClH:22].[CH2:16]([N:17]([CH2:20][CH3:21])[CH2:18][CH2:19][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][N:2]([CH3:1])[CH3:3])[CH3:15]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 13364Diethylaminoethyl chlorideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 328972-((Dimethylamino)methyl)phenol

생성물 1

HCID 18933629HCID 18933629, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 2-(N,N-dimethylaminomethyl)phenol (10.0 g, which contains 30% phenol by weight) in DMF (10 ml) was added dropwise with stirring to a suspension of sodium hydride (3.14 g, 60% dispersion in mineral oil) in DMF (75 ml) at ambient temperature under nitrogen. After the addition the mixture was stirred at ambient temperature for 30 minutes. A solution of 2-chloro-N,N-diethylethylamine in toluene (70 ml) [prepared by dissolving the hydrochloride (14.8 g) in water (20 ml), adding aqueous sodium hydroxide (5M) to basify the mixture and then extracting the mixture with toluene 3×20 ml, drying, filtering and then making up to 70 ml as required] was added dropwise over a period of 2 minutes and the resulting mixture heated on a steam bath for 18 hours under nitrogen. The mixture was poured into ice/water (500 ml) and sodium hydroxide solution was added until the mixture was basic (pH=14). The mixture was extracted with ether to give a residue which was distilled under vacuum. The highest boiling fraction (b.p. 105°-110° C. at 0.6 mbar) was dissolved in ether and acidified with ethereal hydrogen chloride. The solvent was removed under reduced pressure. The residue was dissolved in propan-2-ol and ether added to induce precipitation. The solid was collected by filtration and recrystallised from propan-2-ol to give 2-(2-diethylaminoethoxy)-N,N-dimethylbenzylamine dihydrochloride, m.p. 213°-214° C.

후처리

  1. additionAfter the addition the mixture
  2. extractionextracting the mixture with toluene 3×20 ml
  3. customdrying
  4. filtrationfiltering
  5. additionwas added dropwise over a period of 2 minutes
  6. temperaturethe resulting mixture heated on a steam bath for 18 hours under nitrogen
  7. additionThe mixture was poured into ice/water (500 ml) and sodium hydroxide solution
  8. additionwas added until the mixture
  9. extractionThe mixture was extracted with ether
  10. customto give a residue which
  11. distillationwas distilled under vacuum
  12. dissolutionThe highest boiling fraction (b.p. 105°-110° C. at 0.6 mbar) was dissolved in ether
  13. customThe solvent was removed under reduced pressure
  14. dissolutionThe residue was dissolved in propan-2-ol
  15. additionether added
  16. customprecipitation
  17. filtrationThe solid was collected by filtration
  18. customrecrystallised from propan-2-ol

출처 및 근거

ORD 기록
ord-4e677cedec834d55bb51ea7b4bbf243d
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05736568

반응 노트

불러오는 중…