1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile → [1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamine

HRID 578868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 578868
[Cl:1][C:2]1[C:3]([C:15]2([C:18]#[N:19])[CH2:17][CH2:16]2)=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][CH:9]2[C:11]([F:14])([F:13])[F:12])[CH:7]=1>CO.N.[Ni]>[Cl:1][C:2]1[C:3]([C:15]2([CH2:18][NH2:19])[CH2:17][CH2:16]2)=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][CH:9]2[C:11]([F:14])([F:12])[F:13])[CH:7]=1

Komponenten

5

Edukt 1

HCID 895441591-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile

Produkt 1

HCID 89544472[1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamineAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 222AmmoniaLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

509 mg of 1-[3-chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile (step 2) was dissolved in 35 ml of methanol containing 2 ml of ammonia (7N in methanol). The solution was hydrogenated over Raney-nickel (flow: 1 mL/min, 50° C., 40 bar). Then the solvent was removed at reduced pressure to give 455 mg of [1-[3-chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamine as an orange oil. 1H-NMR (CDCl3): 8.30 ppm (s, 1H), 7.87 ppm (s, 1H), 2.94 ppm (s, 2H), 2.33 ppm (m, 1H), 1.85 ppm (m, 1H), 1.78 ppm (s, 2H, broad), 1.46 ppm (m, 1H), 1.22 ppm (m, 1H), 1.00 ppm (m, 2H), 0.90 ppm (m, 2H).

Aufarbeitung

  1. customThen the solvent was removed at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-30732926b0794f3aafd0ceb40839e207
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040708B2

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