Water → 1-Phenylcyclohexylamine

HRID 366461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 366461
[C:1]1([C:7]2([N:13]=[N+]=[N-])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCOCC1>[C:1]1([C:7]2([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 2769487(1-Azidocyclohexyl)benzene

Produkt 1

HCID 318621-Phenylcyclohexylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The crude azide (18.0 g, ≤96 mmol) was dissolved in dioxane (300 mL) with triphenylphosphine (40 g, 152 mmol) and the stirred solution was refluxed for 4 h. under N2 (g) before adding H2O (9 mL, 0.5 mol). After about 46 h. further reflux, solvent was removed in vacuo at about 45-50° C. and residual moisture was removed by azeotropic distillations in vacuo with CH3CN and Et2O, respectively. The syrupy residue was dissolved in boiling Et2O and chilled to about 0° C. for about 16 h. Precipitated Ph3PO was removed by filtration, and 1M HCl in Et2O (90 mL) was added dropwise at about 5° C. to the etherol filtrate to precipitate the desired 1-phenyl-cyclohexylamine as its HCl salt (12.7 g, LC-MS m/z 162 (MH+)) which was recrystallized from CHCl3 /i-Pr2O before use.

Aufarbeitung

  1. temperaturethe stirred solution was refluxed for 4 h. under N2 (g)
  2. temperatureAfter about 46 h. further reflux
  3. customsolvent was removed in vacuo at about 45-50° C.
  4. customresidual moisture was removed by azeotropic distillations in vacuo with CH3CN and Et2O
  5. dissolutionThe syrupy residue was dissolved
  6. customPrecipitated Ph3PO was removed by filtration, and 1M HCl in Et2O (90 mL)
  7. additionwas added dropwise at about 5° C. to the etherol filtrate
  8. customto precipitate the desired 1-phenyl-cyclohexylamine as its HCl salt (12.7 g, LC-MS m/z 162 (MH+)) which
  9. customwas recrystallized from CHCl3 /i-Pr2O before use

Quellen und Nachweise

ORD-Eintrag
ord-98c5fc8e4cea412ebcc6be85cdda0a18
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130217

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