Sodium Bicarbonate → 1-(3-Cyclohexyl-3-hydroxypropyl)-4-(5-methylpyridin-2-yl)aminopiperidine

HRID 1820301Notes

Reaction equation

HRID 1820301 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1.C(=O)([O-])O.[Na+].BrC1C=CC(S(O[CH2:31][CH2:32][CH:33]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[OH:34])(=O)=O)=CC=1>COCCOC>[CH:35]1([CH:33]([OH:34])[CH2:32][CH2:31][N:12]2[CH2:13][CH2:14][CH:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=3)[CH2:10][CH2:11]2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 207024693-Cyclohexyl-3-hydroxypropyl 4-bromobenzenesulfonateHCID 230210485-Methyl-N-(piperidin-4-YL)pyridin-2-amine

Product 1

HCID 231099131-(3-Cyclohexyl-3-hydroxypropyl)-4-(5-methylpyridin-2-yl)aminopiperidineYield 61.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-(5-methylpyridin-2-yl)aminopiperidine (394 mg, 2 mmol), sodium hydrogencarbonate (277 mg, 3.2 mmol) and 3-cyclohexyl-3-hydroxypropyl 4-bromobenzenesulfonate (932 mg, 2.4 mmol) in 1,2-dimethoxyethane (10 mL) was refluxed for 8 hours. After then adding 5 g of NH silica Chromatorex DM1020 to the reaction mixture, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (60 g NH silica Chromatorex DM2035, hexane:ethyl acetate=1:1) to obtain the title compound as a light yellow solid (405 mg) (59.6% yield).

Workup

  1. temperaturewas refluxed for 8 hours
  2. additionAfter then adding 5 g of NH silica Chromatorex DM1020 to the reaction mixture, it
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (60 g NH silica Chromatorex DM2035, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-72cd5d6c5c3e4117ada0dfd48b567a26
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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