Hydrochloric Acid → 2-Amino-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrile

HRID 896254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896254
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[C:9]([O:21][CH3:22])=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+].Cl>C1COCC1.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[NH2:1][C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]2)[C:9]([O:21][CH3:22])=[CH:8][C:5]=1[C:6]#[N:7]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 223496205-Methoxy-4-[(1-methylpiperidin-4-yl)methoxy]-2-nitrobenzonitrile

Produkt 1

HCID 223496642-Amino-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrileAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-nitro-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrile (1.1 g, 3.6 mmol) in THF (20 ml) in presence of benzyltrimethylammonium chloride (334 mg, 1.8 mmol) was treated by a slow addition of Na2S2O4 (3.1 g, 18 mmol) in water (20 ml). After 0.5 h, HCl (6N, 20 ml) was added to the mixture, which was stirred at 60° C. for 5 h. The mixture was cooled to room temperature, extracted with ethylacetate. The aqueous phase was made basic with Na2 CO3 (solid), and extracted with ethylacetate. The organic phase was dried over MgSO4, concentrated, to give a yellow solid (748 mg, 75%) of title compound.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethylacetate
  3. extractionextracted with ethylacetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-274159f323c348ee8e4688369550225b
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919338B2

Notizen zur Reaktion

Wird geladen…