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

HRID 534159Notes

Reaction equation

HRID 534159 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH:10][CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)[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][CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68385104Tert-butyl 4-(2-(((trans)-2-phenylcyclopropyl)amino)ethyl)piperidine-1-carboxylate

Product 1

HCID 66571640[trans-2-Phenylcyclopropyl][2-(4-piperidinyl)ethyl]amineYield 30.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Chloroform (50 mL) was added to a 200 mL round-bottomed flask containing tert-butyl 4-(2-((trans-2-phenylcyclopropyl)amino)ethyl)piperidine-1-carboxylate (161 mg, 0.467 mmol). HCl/1,4-Dioxane (1 mL, 4.00 mmol) was added and the mixture stirred 18 hours at room temperature. Upon completion, the residue was adsorbed directly onto silica and purified via column chromatography on the ISCO Companion (gradient 0-100% 80:20:2 [CHCl3/MeOH/NH4OH]/CHCl3; 4 g column). Fractions were collected, solvents removed and the resulting residue was taken up in MeOH (2 mL). Excess 2M HCl in Et2O was added and the solution stirred for 10 minutes. The solvent was removed to yield the 2HCl of the desired product (35 mg, 22% yield) as a brown solid: LC-MS (ES) m/z=245 (M+H)+, 1H NMR (400 MHz, MeOH-d4) δ ppm 1.39 (br. s., 1H) 1.51 (br. s., 4H) 1.79 (br. s., 3H) 2.00 (br. s., 2H) 2.61 (br. s., 1H) 3.02 (br. s., 3H) 3.29 (br. s., 1H) 3.35-3.53 (m, 2H) 7.17-7.28 (m, 3H) 7.28-7.36 (m, 2H).

Workup

  1. custompurified via column chromatography on the ISCO Companion (gradient 0-100% 80:20:2 [CHCl3/MeOH/NH4OH]/CHCl3; 4 g column)
  2. customFractions were collected
  3. customsolvents removed
  4. additionExcess 2M HCl in Et2O was added
  5. stirringthe solution stirred for 10 minutes
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-8e796e07df234d66acdcecb0127ca683
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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