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

HRID 529309

Reaction equation

HRID 529309 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-ab8827709e6249e2b826558f69cc42bb
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Linked notes

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