1,4-Dibromobutane → 7-(4-Bromobutoxy)-3-piperidino-2,2-dimethylbenzofuran

HRID 3776

Reaktionsgleichung

Reaktionsgleichung von HRID 3776
[OH-].[K+].[OH:3][C:4]1[C:12]2[O:11][C:10]([CH3:14])([CH3:13])[CH:9]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1.[Br:21][CH2:22][CH2:23][CH2:24][CH2:25]Br>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC>[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][O:3][C:4]1[C:12]2[O:11][C:10]([CH3:13])([CH3:14])[CH:9]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 80561,4-DibromobutaneHCID 14797Potassium HydroxideHCID 141266507-Hydroxy-3-piperidino-2,2-dimethylbenzofuran

Produkt 1

HCID 212890017-(4-Bromobutoxy)-3-piperidino-2,2-dimethylbenzofuran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Crushed potassium hydroxide (19.6 g) and tetrabutyl ammonium chloride (1.7 g) are added to a solution of 7-hydroxy-3-piperidino-2,2-dimethylbenzofuran (14.4 g) in 1,4-dibromobutane (69.4 ml) and the mixture stirred at RT under nitrogen for 5 hours. The reaction mixture is diluted with ether, washed with water, extracted with 5% aq. HCl and the acidic phase washed with ether. The acidic phase is made basic thereby forming an oil which is taken up in ether, washed with sat'd aq. NaCl, dried, filtered and evaporated in vacuo affording the desired product as a liquid.

Aufarbeitung

  1. washwashed with water
  2. extractionextracted with 5% aq. HCl
  3. washthe acidic phase washed with ether
  4. customThe acidic phase is made basic thereby forming an oil which
  5. washwashed with sat'd aq. NaCl
  6. customdried
  7. filtrationfiltered
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e1cc7aae472c4f0e89601c6881976e37
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04722925

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