Tetralin → 7-Benzyl-3-isopropyl-3,7-diazabicyclo[3.3.1]nonane

HRID 1195220

Reaktionsgleichung

Reaktionsgleichung von HRID 1195220
[OH-].[K+].[CH2:3]([N:10]1[CH2:17][CH:16]2[C:18](=O)[CH:12]([CH2:13][N:14]([CH:20]([CH3:22])[CH3:21])[CH2:15]2)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.NN.C1C2C(=CC=CC=2)CCC1>C(O)COCCOCCO.O>[CH2:3]([N:10]1[CH2:11][CH:12]2[CH2:18][CH:16]([CH2:15][N:14]([CH:20]([CH3:22])[CH3:21])[CH2:13]2)[CH2:17]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 8404TetralinHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 3671713-Benzyl-7-isopropyl-3,7-diazabicyclo[3.3.1]nonan-9-one

Produkt 1

HCID 99506987-Benzyl-3-isopropyl-3,7-diazabicyclo[3.3.1]nonane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8172Triethylene GlycolLösungsmittel

Versuchsvorschrift

To a mixture of KOH pellets (85%, 11.62 g, 176 mmol) and the ketone (21) (6.0 g, 22 mmol) in triethylene glycol (100 mL) was added hydrazine (95%, 2.97 g, 88 mmol) in one portion in a 200-mL, jacketed flask equipped with a magnetic stirrer, a heating mantle, a standard condenser, a lower take-off condenser with a N2 inlet, and two glass stoppers. A heating temperature of 200°-210° C. for 4 h under N2 was produced by boiling tetralin (bp 207° C.) in the jacket. Cooling of the solution to RT was followed by the addition of chilled water (125 mL). Combined extracts (ether, 4×50 mL) of the suspension were washed with 10% NaOH (50 mL) and saturated NaCl (50 mL), dried (Na2SO4, 1 h), filtered, and concentrated (rotary evaporator then vacuum pump, overnight, RT/0.2 mm Hg) to a yellow oil (5.53 g, 97.3%). Analysis of the very slight crude amine (30) showed no carbonyl stretch in the IR spectrum, and thus it was used without further purification.

Aufarbeitung

  1. customequipped with a magnetic stirrer
  2. customA heating temperature of 200°-210° C. for 4 h under N2 was produced
  3. washCombined extracts (ether, 4×50 mL) of the suspension were washed with 10% NaOH (50 mL) and saturated NaCl (50 mL)
  4. dry with materialdried (Na2SO4, 1 h)
  5. filtrationfiltered
  6. concentrationconcentrated (
  7. customrotary evaporator
  8. customvacuum pump, overnight, RT/0.2 mm Hg
  9. customwas used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-a72ddddbb82141b38a89a94d7a6bb3ef
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05110933

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