Hydrochloric Acid → (trans)-2-(3'-(Trifluoromethyl)biphenyl-4-yl)cyclopropanamine hydrochloride

HRID 1470551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470551
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[CH2:17][C@H:16]3[NH:18]C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[ClH:28]>C(OCC)C>[ClH:28].[F:1][C:2]([F:26])([F:27])[C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[CH2:17][C@H:16]3[NH2:18])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86673371Tert-butyl(trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylcarbamate

Produkt 1

HCID 66715450(trans)-2-(3'-(Trifluoromethyl)biphenyl-4-yl)cyclopropanamine hydrochlorideAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl (trans)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropylcarbamate (200 mg, 0.53 mmol), in diethyl ether (5 mL) at 10° C. was added HCl in diethyl ether (3 mL), slowly dropwise over a period of 10 min, stirred the reaction mixture for 4 h. After completion, the solvent was evaporated, residue was triturated with hexane (5 mL) and diethyl ether (5 mL), and dried under reduced pressure to get (trans)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropanamine hydrochloride (140 mg, 77.8%) as a white solid. 1H-NMR (DMSO-d6) δ (ppm): 1.27 (q, 1H), 1.46 (quin, 1H), 2.41 (m, 1H), 2.86 (m, 1H), 7.29 (d, 2H), 7.69 (m, 4H), 7.96 (m, 2H), 8.53 (s, 1H), 8.61 (br, 2H). MS (M+H): 278.3

Aufarbeitung

  1. customAfter completion, the solvent was evaporated
  2. customresidue was triturated with hexane (5 mL) and diethyl ether (5 mL)
  3. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5978d706fc884e95ab090ad5db342a56
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006449B2

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