Diisopropylamine → 2-[1-(Cyclohexylmethyl)piperidin-4-ylamino]-5-methylpyridine

HRID 2223877Notes

Reaction equation

HRID 2223877 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=2)[CH2:3][CH2:2]1.C(NC(C)C)(C)C.[CH:22]1([CH2:28]Br)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(OCC)(=O)C>C(O)C>[CH:22]1([CH2:28][N:1]2[CH2:6][CH2:5][CH:4]([NH:7][C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=3)[CH2:3][CH2:2]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 137636Cyclohexane, (bromomethyl)-HCID 230210485-Methyl-N-(piperidin-4-YL)pyridin-2-amine

Product 1

HCID 230210002-[1-(Cyclohexylmethyl)piperidin-4-ylamino]-5-methylpyridineYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(piperidin-4-ylamino)-5-methylpyridine (191 mg), diisopropylamine (202 mg) and cyclohexylmethyl bromide (212 mg) in ethanol (2 mL) was refluxed for 16 hours. To the reaction solution was added ethyl acetate, and insolubles were filtered off, and then, concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (NH silica gel, hexane:ethyl acetate=4:1) to give the title compound (216 mg).

Workup

  1. filtrationwere filtered off
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel chromatography (NH silica gel, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-92a28647c07c4764a24557189ce4a028
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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