1,4-Dioxane hydrochloride → [trans-2-Phenylcyclopropyl][1-(4-piperidinyl)ethyl]amine

HRID 534161

Reaktionsgleichung

Reaktionsgleichung von HRID 534161
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH:10][CH:11]([CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O1CCOCC1>C(Cl)(Cl)Cl>[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH:10][CH:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH3:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 204431481,4-Dioxane hydrochlorideHCID 683852361,1-Dimethylethyl 4-(1-{[trans-2-phenylcyclopropyl]amino}ethyl)-1-piperidinecarboxylate

Produkt 1

HCID 66571641[trans-2-Phenylcyclopropyl][1-(4-piperidinyl)ethyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Chloroform (5 mL) was added to a 200 mL round-bottomed flask containing 1,1-dimethylethyl 4-(1-{[trans-2-phenylcyclopropyl]amino}ethyl)-1-piperidinecarboxylate (67 mg, 0.194 mmol) to give a suspension. HCl/1,4-Dioxane (1.5 mL, 6.00 mmol) was added and the mixture stirred 18 hours at room temperature. The Upon completion, the solvents were removed, MeOH (1 mL) added and the mixture purified via reverse phase column chromatography on Gilson ((C18 column: 0.1% Formic acid H2O/CH3CN, 95-5%) affording the title compound as a white solid LC-MS (ES) m/z=245 (M+H)+, 1H NMR (400 MHz, MeOD-d4) δ ppm 1H NMR (400 MHz, MeOD) d 7.93 (s, 1H), 7.31-7.39 (m, 2H), 7.17-7.30 (m, 3H), 3.46-3.59 (m, 3H), 2.95-3.14 (m, 3H), 2.50-2.63 (m, 1H), 2.17-2.28 (m, 1H), 1.94-2.05 (m, 3H), 1.59-1.76 (m, 3H), 1.48 (t, J=7.71 Hz, 1H), 1.39 (d, J=6.82 Hz, 3H).

Aufarbeitung

  1. customto give a suspension
  2. customThe Upon completion, the solvents were removed
  3. additionMeOH (1 mL) added
  4. customthe mixture purified via reverse phase column chromatography on Gilson ((C18 column: 0.1% Formic acid H2O/CH3CN, 95-5%)

Quellen und Nachweise

ORD-Eintrag
ord-2ecc2ecd0bd345f8b4cde707c4c84f36
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853408B2

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