Hydrochloric Acid → 2-((2,6-Dimethylpiperidino)amino)-3-phenylpropionitrile

HRID 1646385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1646385
[C-:1]#[N:2].[Na+].[C:4]1([CH2:10][CH:11]=O)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:13][N:14]1[CH:19]([CH3:20])[CH2:18][CH2:17][CH2:16][CH:15]1[CH3:21].Cl>O.CO>[CH3:21][CH:15]1[CH2:16][CH2:17][CH2:18][CH:19]([CH3:20])[N:14]1[NH:13][CH:11]([CH2:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]#[N:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 998PhenylacetaldehydeHCID 8929Sodium CyanideHCID 1234822,6-Dimethyl-1-piperidylamine

Produkt 1

HCID 198020412-((2,6-Dimethylpiperidino)amino)-3-phenylpropionitrileAusbeute 126,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

7.4 g of sodium cyanide, dissolved in 40 ml of water, and 18.0 g of phenyl acetaldehyde, dissolved in 30 ml of methanol, are added dropwise with ice-cooling to a mixture of 12.8 g of 1-amino-2,6-dimethylpiperidine, 60 ml of water and 8.6 ml of concentrated hydrochloric acid. The reaction mixture is stirred at room temperature for 3 days and extracted with dichloromethane. The combined organic phases are washed with water of pH 4-5 containing acetic acid, dried and concentrated in a rotary evaporator. 32.5 g of 2-((2,6-dimethylpiperidino)amino)-3-phenylpropionitrile are obtained, which are reacted further without further purification.

Aufarbeitung

  1. additionare added dropwise with ice-
  2. extractionextracted with dichloromethane
  3. washThe combined organic phases are washed with water of pH 4-5
  4. additioncontaining acetic acid
  5. customdried
  6. concentrationconcentrated in a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-b0ebf0c816a74375901406c2b462383c
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05179206

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