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

HRID 534159

反応式

HRID 534159 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8e796e07df234d66acdcecb0127ca683
出典データセット
uspto-grants-2014_10
特許番号
US08853408B2

関連ノート

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