Diisopropylethylamine → N-Benzyl-N-methyl-2-(1-(pyridin-4-yl)piperidin-4-yl)ethanamine

HRID 1193337Notes

Reaction equation

HRID 1193337 reaction equation
[CH2:1]([N:8]([CH3:17])[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:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C>C(O)CCC>[CH2:1]([N:8]([CH3:17])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 19085399N-Benzyl-N-methyl-2-(piperidin-4-yl)ethanamineHCID 446301274-Bromopyridine Hydrobromide

Product 1

HCID 66799326N-Benzyl-N-methyl-2-(1-(pyridin-4-yl)piperidin-4-yl)ethanamineYield 56%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

N-Benzyl-N-methyl-2-(piperidin-4-yl)ethanamine (600 mg, 2.58 mmol, 1 eq) and 4-bromo-pyridine HBr (553 mg, 2.84 mmol, 1.1 eq) were dissolved in n-butanol (15 ml); DIPEA (2.34 ml, 12.9 mmol, 5 eq) was added, and refluxing was carried out for 16 h. After monitoring by thin-layer chromatography, the reaction mixture was concentrated and the residue was purified by column chromatography (Alox 5-7% MeOH in dichloromethane). Yield: 56% (450 mg, 1.45 mmol).

Workup

  1. temperaturerefluxing
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by column chromatography (Alox 5-7% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-011806fac0054f42bfaeae053a1628e3
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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