2-(Dimethylamino)ethanol → (6-Chloropyridin-2-yl)(1-methylpiperidin-4-yl)methanone

HRID 404224

Reaction equation

HRID 404224 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.CN(C)CCO.CON(C)[C:22]([CH:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1)=[O:23]>CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:22]([CH:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[O:23])[N:3]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 79772-ChloropyridineHCID 23499459N-Methoxy-N,1-dimethylpiperidine-4-carboxamideHCID 178418339Butyllithium

Product 1

HCID 10705139(6-Chloropyridin-2-yl)(1-methylpiperidin-4-yl)methanoneYield 47.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

Add 2-chloropyridine (1 g, 8.8 mmole) to a mixture of n-butyl lithium (1.6 M in hexane) (22 mL, 35.2 mmole) and 2-dimethylamino-ethanol (1.56 g, 17.6 mmole) in hexane (20 mL at −78° C.) and stirred for 1 hour. Then add 1-methyl-piperidine-4-carboxylic acid methoxy-methyl-amide (3.2 g, 17.6 mmole) in hexane (5 mL) and stir the mixture for 1 hour. Quench the reaction mixture with water and extract twice with ethyl acetate, dry the organic layer with anhydrous sodium sulfate, evaporate the solvent and purify the residual product by chromatography on a silica gel column to give about 1 g of the title product.

Workup

  1. customQuench the reaction mixture with water
  2. extractionextract twice with ethyl acetate
  3. dry with materialdry the organic layer with anhydrous sodium sulfate
  4. customevaporate the solvent
  5. custompurify the residual product by chromatography on a silica gel column

Sources & evidence

ORD record
ord-aba5696c17414b9991c86a87aeb18a46
Source dataset
uspto-grants-2014_06
Patent number
US08748459B2

Linked notes

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