Sodium Sulfate → 3'-beta-Aminoethylidene-spiro(cyclopentane-1,1'-indan)

HRID 426919

Reaktionsgleichung

Reaktionsgleichung von HRID 426919
[C:1]12([CH2:16][CH2:15][CH2:14][CH2:13]1)[C:9]1[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:3](=[CH:10][C:11]#[N:12])[CH2:2]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[NH2:12][CH2:11][CH:10]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:2]1

Komponenten

6

Edukt 4

HCID 24436Sodium SulfateHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 54124997Spiro(cyclopentane-1,1'-indan)-3'-ylideneacetonitrile

Produkt 1

HCID 540829983'-beta-Aminoethylidene-spiro(cyclopentane-1,1'-indan)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of spiro(cyclopentane-1,1'-indan)-3'-ylideneacetonitrile (10.5 g; 0.05 moles) in anhydrous ether (100 ml) is added dropwise under agitation to lithium aluminum hydride (2.5 g; 0.066 moles) suspended in ether (200 ml). After boiling for 3 hours the mixture is cooled to room temperature and the excess of hydride is decomposed by dropwise addition of a saturated sodium sulphate solution. The precipitate obtained is filtered off and washed with ether. The ether solutions are shaken with 2 N hydrochloric acid. The acid extracts are concentrated to a small volume in vacuum (bath temperature below 40° C.) and the amine hydrochloride is precipitated by treatment with conc. hydrochloric acid in the cooled. Yield 10.6 g (85%). Recrystallization from 2-propanol yields colourless crystals of mp. 190° C. identical with the product prepared according to example 3g.

Aufarbeitung

  1. customThe precipitate obtained
  2. filtrationis filtered off
  3. washwashed with ether
  4. concentrationThe acid extracts are concentrated to a small volume in vacuum (bath temperature below 40° C.)
  5. customthe amine hydrochloride is precipitated by treatment with conc. hydrochloric acid in the cooled
  6. customRecrystallization from 2-propanol
  7. customyields colourless crystals of mp. 190° C. identical with the product
  8. customprepared

Quellen und Nachweise

ORD-Eintrag
ord-16b0d6a7dd3a44aaa813ec73ce084db6
Quelldatensatz
uspto-grants-1979_10
Patentnummer
US04172093

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