Dibenzylamine → tert-Butyl 4-(2-(dibenzylamino)ethyl)piperidine-1-carboxylate

HRID 1193298Notes

Reaction equation

HRID 1193298 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O[CH2:21][CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)(=O)=O.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:21][CH2:22][CH:23]1[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:27][CH2:28]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 8471TriethylamineHCID 15229596tert-Butyl 4-(2-((methanesulfonyl)oxy)ethyl)piperidine-1-carboxylate

Product 1

HCID 66805425tert-Butyl 4-(2-(dibenzylamino)ethyl)piperidine-1-carboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dibenzylamine (4.1 ml, 21.24 mmol, 1 eq) was added to a solution of tert-butyl 4-(2-(methyl-sulfonyloxy)ethyl)piperidine-1-carboxylate (6.5 g, 21.24 mmol, 1 eq) and triethylamine (3.2 ml, 23.36 mmol, 1.1 eq) in toluene (100 ml), and refluxing was carried out for 72 h. Then the reaction solution was concentrated and the residue was taken up in dichloromethane (300 ml), washed with water and sat. NaCl solution (in each case 100 ml), dried over sodium sulfate and concentrated under reduced pressure. After purification by column chromatography (silica gel, 5% ethyl acetate in hexane), a yellow solid was obtained. Yield: 67% (5.8 g, 14.21 mmol).

Workup

  1. temperaturerefluxing
  2. concentrationThen the reaction solution was concentrated
  3. washwashed with water and sat. NaCl solution (in each case 100 ml),
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customAfter purification by column chromatography (silica gel, 5% ethyl acetate in hexane)
  7. customa yellow solid was obtained

Sources & evidence

ORD record
ord-4cc2b2a20ff14f23b3eabd4e519d81e0
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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