Diisopropylethylamine → N,N-Dibenzyl-2-(1-(pyridin-4-yl)piperidin-4-yl)ethanamine

HRID 1193300Notes

Reaction equation

HRID 1193300 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.Br[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C>C(O)CCC>[CH2:17]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:15][CH2:16]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 446301274-Bromopyridine HydrobromideHCID 66798731(Dibenzyl) [2-(4-piperidyl)ethyl]amine

Product 1

HCID 66799257N,N-Dibenzyl-2-(1-(pyridin-4-yl)piperidin-4-yl)ethanamineYield 53%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

N,N-Dibenzyl-2-(piperidin-4-yl)ethanamine (2.4 g, 7.79 mmol, 1 eq) and 4-bromopyridine HBr (1.97 g, 10.12 mmol, 1.3 eq) were dissolved in n-butanol (30 ml) and DIPEA (3.3 ml, 19.47 mmol, 2.5 eq) and the mixture was refluxed for 48 h. After monitoring by thin-layer chromatography, the reaction solution was concentrated under reduced pressure and the residue was taken up in dichloromethane (100 ml), washed with water and sat. NaCl solution (in each case 50 ml), dried over sodium sulfate and concentrated under reduced pressure. After purification by column chromatography (silica gel, 3.5% MeOH in dichloromethane), a white solid was obtained. Yield: 53% (1.6 g, 4.15 mmol).

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. washwashed with water and sat. NaCl solution (in each case 50 ml),
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customAfter purification by column chromatography (silica gel, 3.5% MeOH in dichloromethane)
  6. customa white solid was obtained

Sources & evidence

ORD record
ord-46feede4f6bd453f891f58330bae694d
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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