Hydrochloric Acid → trans-1-[3-(Dimethylamino)propyl]-2-indanol

HRID 427105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 427105
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.B.[OH-:17].[Na+].OO.Cl>O1CCCC1.O.C(O)C>[CH3:15][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@H:7]1[OH:17]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 230024761(N,N-dimethylaminopropyl)indene

Produkt 1

HCID 54288417trans-1-[3-(Dimethylamino)propyl]-2-indanolAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 20.6 g (0.10 mole) of 1-[3-(dimethylamino)-propyl]-indene in 100 ml of tetrahydrofuran is cooled to 0° under nitrogen and 200 ml of 1 M borane in tetrahydrofuran added over 30 minutes. After stirring overnight at ambient temperature the solution is cooled to 0° and the following added in the given order: 30 ml of water added cautiously, 170 ml of 10% sodium hydroxide solution and 32 ml of 30% hydrogen peroxide solution. After 1 hour at 0° the mixture is diluted with 1 liter of water and extracted with chloroform (3×400 ml) to give a white solid which is refluxed with 300 ml each of ethanol and 5% hydrochloric acid for 1 hour. After addition of 300 ml of water, 400 ml of distillate is collected. The residue is cooled, extracted with chloroform (200 ml, discard), basified with excess sodium hydroxide and extracted with chloroform (3×300 ml). Drying and solvent removal give 17.6 g of oil (81%, 1 spot on TLC).

Aufarbeitung

  1. temperatureis cooled to 0°
  2. additionthe following added in the given order
  3. extractionextracted with chloroform (3×400 ml)
  4. customto give a white solid which
  5. customis collected
  6. temperatureThe residue is cooled
  7. extractionextracted with chloroform (200 ml, discard)
  8. extractionextracted with chloroform (3×300 ml)
  9. customDrying
  10. customsolvent removal

Quellen und Nachweise

ORD-Eintrag
ord-7ff1c8817f774485aedf730a77c430a1
Quelldatensatz
uspto-grants-1979_10
Patentnummer
US04172945

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