Benzylamine → 3-Benzylamino-1-indanol

HRID 65838

Reaktionsgleichung

Reaktionsgleichung von HRID 65838
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[CH2:11]1>CCOCC>[CH2:1]([NH:8][CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]([OH:19])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 117459123-Bromo-1-indanone

Produkt 1

HCID 227560943-Benzylamino-1-indanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Cool a solution of benzylamine (3.22 g.) in dry ether (25 ml.) to below 0° C. With stirring under nitrogen add a cooled (below 0° C.) solution of 3-bromo-1-indanone (3.17 g.) in ether (25 ml.) dropwise over 1.5 hours. Store the reaction under nitrogen at -10° C. for one day. Quickly filter the cold solution and add it cold to a stirring solution of one molar borane in tetrahydrofuran (60 ml.) below 0° C. and under nitrogen. Stir the solution for 18 hours at room temperature. Carefully add a solution of water (3.24 ml.) in tetrahydrofuran (20 ml.) dropwise, followed by 8.0 ml. of 5M isopropanolic --HCl, and continue stirring overnight. Store the reaction at -10° C. overnight, then filter the precipitate through filter-aid. Extract the dry solid mixture with methanol-methylene chloride, filter and evaporate the solvents in vacuo. Triturate the resulting solid with cold ethyl acetate, filter and dry to obtain 2.36 g. of the title product as the hydrochloride salt, m.p. 233-235°. λmaxKBr 3.0 μ (OH).

Aufarbeitung

  1. additionadd
  2. customStore the reaction under nitrogen at -10° C. for one day
  3. filtrationQuickly filter the cold solution
  4. additionadd it cold to a stirring solution of one molar borane in tetrahydrofuran (60 ml.) below 0° C.
  5. stirringStir the solution for 18 hours at room temperature
  6. additionCarefully add a solution of water (3.24 ml.) in tetrahydrofuran (20 ml.) dropwise
  7. stirringof 5M isopropanolic --HCl, and continue stirring overnight
  8. customStore the reaction at -10° C. overnight
  9. filtrationfilter the precipitate
  10. filtrationthrough filter-aid
  11. extractionExtract the dry solid mixture with methanol-methylene chloride
  12. filtrationfilter
  13. customevaporate the solvents in vacuo
  14. customTriturate the resulting solid with cold ethyl acetate
  15. filtrationfilter
  16. customdry
  17. customto obtain 2.36 g

Quellen und Nachweise

ORD-Eintrag
ord-d1550dc8f84e476d99984a492aceb7c5
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04129561

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