Diisopropylethylamine → HCID 66799123, compound

HRID 1193323Notes

Reaction equation

HRID 1193323 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH3:17])[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][C:10]2([CH3:16])[CH3:15])=[CH:5][CH:4]=1.Cl.Br[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>C(O)CCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH3:17])[CH:9]2[CH2:14][CH2:13][N:12]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH2:11][C:10]2([CH3:16])[CH3:15])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 881004-Bromopyridinium chlorideHCID 66799374HCID 66799374, compound

Product 1

HCID 66799123HCID 66799123, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

N-(4-Methoxybenzyl)-N,3,3-trimethylpiperidin-4-amine (5.17 mmol, 1 eq) and 4-bromopyridine hydrochloride (1.509 g, 7.76 mmol, 1.5 eq) were dissolved in n-butanol (40 ml) and DIPEA (4.26 ml, 25.87 mmol, 5 eq) and refluxed for 16 h. After monitoring by thin-layer chromatography, the reaction solution was concentrated under reduced pressure. After purification by column chromatography (silica gel, 5% MeOH in dichloromethane), the desired product was obtained in the form of a white solid. Yield: 40% (700 mg, 2.06 mmol).

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customAfter purification by column chromatography (silica gel, 5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-c7bd74e9098141f4b0fefa217ae78276
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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