Sodium Hydroxide → Piperidine, 1-methyl-4-phenoxy-4-phenyl-

HRID 1156029

Reaktionsgleichung

Reaktionsgleichung von HRID 1156029
N([O-])=O.[Na+].N[C:6]1[CH:25]=[CH:24][C:9]([O:10][C:11]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:8][CH:7]=1.[PH2](O)=O.[OH-].[Na+]>O.Cl>[CH3:17][N:14]1[CH2:15][CH2:16][C:11]([O:10][C:9]2[CH:24]=[CH:25][CH:6]=[CH:7][CH:8]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12][CH2:13]1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 3060392Piperidine, 4-(p-aminophenoxy)-1-methyl-4-phenyl-HCID 4124402Phosphinic AcidHCID 23668193Sodium Nitrite

Produkt 1

HCID 3060394Piperidine, 1-methyl-4-phenoxy-4-phenyl-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

A solution of 3.0 g of sodium nitrite in 18 ml of water is added dropwise to a solution of 10.0 g of 4-(4-aminophenoxy)-1-methyl-4-phenylpiperidine in 12 ml of concentrated hydrochloric acid and 30 ml of water at -10° C. The mixture is subsequently stirred at -5° C. for 45 minutes, 50 ml of 50% strength hypophosphorous acid are added dropwise at -5° C., and the reaction mixture is left to stand at 0° C. for 24 hours. It is rendered alkaline with 6 N sodium hydroxide solution, while cooling with ice, and extracted with diethyl ether. After treating the organic phase with active charcoal, it is dried over sodium sulfate and concentrated. Resulting residue yields (after recrystallization from 100 ml of n-hexane) 5.5 g of the title compound of m.p. 99° to 101° C.

Aufarbeitung

  1. waitthe reaction mixture is left
  2. waitto stand at 0° C. for 24 hours
  3. temperaturewhile cooling with ice
  4. extractionextracted with diethyl ether
  5. additionAfter treating the organic phase with active charcoal, it
  6. dry with materialis dried over sodium sulfate
  7. concentrationconcentrated
  8. customResulting residue yields
  9. custom(after recrystallization from 100 ml of n-hexane) 5.5 g of the title compound of m.p. 99° to 101° C.

Quellen und Nachweise

ORD-Eintrag
ord-273e84636d54429ab569ae05df80628b
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04333942

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