Hydrochloric Acid → Tert-butyl 4-[3-(propylamino)pyridin-2-yl]piperazine-1-carboxylate

HRID 1449705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449705
C([BH3-])#N.[Na+].[CH3:5][C:6]([CH3:24])([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10])[CH3:7].[CH3:25][CH2:26][CH:27]=O.Cl.[OH-].[NH4+]>ClCCl.CO>[CH3:7][C:6]([CH3:24])([O:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[C:22]([NH:23][CH2:25][CH2:26][CH3:27])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:15][CH2:16]1)=[O:10])[CH3:5]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 527PropanalHCID 14923Ammonium HydroxideHCID 2756375tert-Butyl 4-(3-aminopyridin-2-yl)piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 21477648Tert-butyl 4-[3-(propylamino)pyridin-2-yl]piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sodium cyanoborohydride (0.31 g) is added to a cold solution of 1-[1,1dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine (International Publication No. WO 88/08424, 2.8 g), propional (0.87 g), and methanol (15 ml). After the exotherm has subsided, the reaction is stirred at 20°-25° overnight. The reaction is acidified (pH 2) with aqueous hydrochloride and then diluted with dichloromethane. The pH is adjusted with aqueous ammonium hydroxide (pH 8), and the phases are separated. The organic phase is dried over sodium sulfate, and concentrated under reduced pressure to a crude product which is dissolved in diethyl ether and allowed to crystallize at -5°. The solid is identified as starting material. The mother liquor is concentrated in vacuo to give the title compound.

Aufarbeitung

  1. customthe phases are separated
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure to a crude product which
  4. dissolutionis dissolved in diethyl ether
  5. customto crystallize at -5°
  6. concentrationThe mother liquor is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d2688b79dc114d39b78fb6c840a195ea
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599930

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