Sodium Hydroxide → N-ethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine hydrochloride

HRID 1194453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1194453
[BH4-].[Na+].[Cl:3][C:4]1C=C(C2(C(N)C)CCC2)C=C[C:9]=1Cl.Cl.[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2([CH:31]([NH2:33])[CH3:32])[CH2:30][CH2:29][CH2:28]2)[CH:23]=[CH:24][C:25]=1[Cl:26].[OH-].[Na+]>C(O)(=O)C>[ClH:3].[CH2:4]([NH:33][CH:31]([C:27]1([C:22]2[CH:23]=[CH:24][C:25]([Cl:26])=[C:20]([Cl:19])[CH:21]=2)[CH2:30][CH2:29][CH2:28]1)[CH3:32])[CH3:9]

Komponenten

6

Edukt 4

HCID 14798Sodium Hydroxide2×HCID 4311764Sodium borohydrideHCID 130831401-[1-(3,4-Dichlorophenyl)cyclobutyl]ethylamineHCID 130831411-[1-(3,4-Dichlorophenyl)cyclobutyl]ethylamine hydrochloride

Produkt 1

HCID 13083301N-ethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Sodium borohydride (2.0 g) was added to solution of 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine (1.5 g prepared by treating the product of Example 1 with aqueous sodium hydroxide) in glacial acetic acid (30 ml). The mixture was heated at 95°-100° C. for sixteen hours and then cooled. Aqueous sodium hydroxide solution was added and the reaction mixture extracted with ether. The ther extract was shaken with 5N hydrochloric acid and the aqueous layer was washed with ether, basified and extracted with ether. Hydrogen chloride gas was passed into the ether extract which was evaporated to dryness. Trituration with acetone gave N-ethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine hydrochloride (m.p. 211°-212° C.). (Formula I R1 =Me, R2 =H; R3 =Et; R4 =H; R5 =4-Cl and R6 =3- Cl.)

Aufarbeitung

  1. customprepared
  2. temperatureThe mixture was heated at 95°-100° C. for sixteen hours
  3. temperaturecooled
  4. extractionthe reaction mixture extracted with ether
  5. extractionThe ther extract
  6. washthe aqueous layer was washed with ether
  7. extractionextracted with ether
  8. extractionextract which
  9. customwas evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1948ace1060c4172bf9bb6a25a251925
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04814352

Notizen zur Reaktion

Wird geladen…