Pentyl nitrite → Piperidine, 1-methyl-4-phenoxy-4-phenyl-

HRID 2285919

Reaktionsgleichung

Reaktionsgleichung von HRID 2285919
N[C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.N(OCCCCC)=O>C1COCC1>[CH3:13][N:10]1[CH2:11][CH2:12][C:7]([O:6][C:5]2[CH:20]=[CH:21][CH:2]=[CH:3][CH:4]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:9]1

Komponenten

4

Edukt 2

HCID 10026Pentyl nitrite2×HCID 3060392Piperidine, 4-(p-aminophenoxy)-1-methyl-4-phenyl-

Produkt 1

HCID 3060394Piperidine, 1-methyl-4-phenoxy-4-phenyl-Ausbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 4-(4-aminophenoxy)-1-methyl-4-phenylpiperidine (2.82 g, 10 mM), in THF (75 ml) was added over 2 hours to a refluxing solution of amyl nitrite (2.7 ml, 20 mM) in THF (30 ml). After 5 hours at reflux amyl nitrite (1.5 ml) was added and the mixture maintained at reflux for 24 hours. The solvent was removed under reduced pressure and the residue partitioned between 2 N hydrochloric acid (50 ml) and ether (50 ml). The aqueous phase was basified (pH9) and extracted with ether (2×100 ml). The organic phase was dried and the solvents removed under reduced pressure. Sublimation of the residue at 1.0 mbar pressure (bath temp. 100°) gave the title compound (700 mg), m.p. 103°-4°.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture maintained
  3. temperatureat reflux for 24 hours
  4. customThe solvent was removed under reduced pressure
  5. customthe residue partitioned between 2 N hydrochloric acid (50 ml) and ether (50 ml)
  6. extractionextracted with ether (2×100 ml)
  7. customThe organic phase was dried
  8. customthe solvents removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ec005ad339844366b79f7d9d4f6194ef
Quelldatensatz
uspto-grants-1982_04
Patentnummer
US04325953

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