Hydrochloric Acid → 2-[2-(4-chloro-alpha,alpha-dimethylbenzylamino) ethoxy]-N,N-dimethylbenzylamine dihydrochloride hemihydrate

HRID 1598307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1598307
B.C1C[O:5]CC1.[Cl:7][C:8]1[CH:32]=[CH:31][C:11]([C:12]([NH:15][C:16](=O)[CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25](=O)[N:26]([CH3:28])[CH3:27])([CH3:14])[CH3:13])=[CH:10][CH:9]=1.[ClH:33]>C1COCC1.CCOCC>[OH2:5].[ClH:7].[ClH:33].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][N:26]([CH3:27])[CH3:28])([CH3:14])[CH3:13])=[CH:31][CH:32]=1.[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][N:26]([CH3:27])[CH3:28])([CH3:14])[CH3:13])=[CH:31][CH:32]=1.[ClH:7].[ClH:7]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 18933598N-(4-chloro-alpha,alpha-dimethylbenzyl)-2-(2-dimethylcarbamoyl-phenoxy)acetamide

Produkt 1

HCID 1317205912-[2-(4-chloro-alpha,alpha-dimethylbenzylamino) ethoxy]-N,N-dimethylbenzylamine dihydrochloride hemihydrate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of borane/THF (27 ml, 1M solution) was added to a solution of N-(4-chloro-α,α-dimethylbenzyl)-2-(2-dimethylcarbamoylphenoxy)acetamide (2.0 g) in THF (20 ml) at 0° C. with stirring under a nitrogen atmosphere. The mixture was warmed to ambient temperature and then boiled under reflux for 1 hour. The mixture was evaporated to dryness and 2M hydrochloric acid (50 ml) was added carefully. The mixture was heated on a steam bath for 2 hours, then cooled, washed with ethyl acetate, basified with 2M sodium hydroxide solution and extracted into dichloromethane to give an oil which was distilled under high vacuum to give an oil, b.p. 150° C. at 0.13 mbar. The oil was dissolved in ether and acidified with ethereal hydrogen chloride. The precipitate was collected by filtration to give 2-[2-(4-chloro-α,α-dimethylbenzylamino) ethoxy]-N,N-dimethylbenzylamine dihydrochloride hemihydrate m.p. 140° C. (with effervescence).

Aufarbeitung

  1. temperatureunder reflux for 1 hour
  2. customThe mixture was evaporated to dryness and 2M hydrochloric acid (50 ml)
  3. additionwas added carefully
  4. temperatureThe mixture was heated on a steam bath for 2 hours
  5. temperaturecooled
  6. washwashed with ethyl acetate
  7. extractionextracted into dichloromethane
  8. customto give an oil which
  9. distillationwas distilled under high vacuum
  10. customto give an oil, b.p. 150° C. at 0.13 mbar
  11. filtrationThe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-76e144322c96464eb60fa8678a5075e5
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05736568

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