1-Bromo-3-chloropropane → 2-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridine

HRID 551583Notes

Reaction equation

HRID 551583 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:10][CH:11]=1.[N:19]1(CC2N=CC(O)=CC=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.BrCCCCl.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[N:13]1([CH2:12][C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:11][N:10]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 445154576-Piperidin-1-ylmethyl-pyridin-3-olHCID 67188055HCID 67188055, compound

Product 1

HCID 111745632-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridineYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

5-(3-Chloro-propoxy)-2-Piperidin-1ylmethyl-pyridine. A solution of 6-piperidin-1-ylmethyl-pyridin-3-ol (0.225 g, 1.17 mmol), 1-bromo-3-chloro propane (0.23 mL, 2.34 mmol), and K2CO3 (0.483 g, 3.50 mmol) in acetone (10 mL) was heated to reflux temperature. After 10 h the reaction mixture was cooled to rt, diluted with acetone (50 mL) and filtered through a pad of diatomaceous earth. The filtrate was concentrated, giving the crude title compound as an oil (0.250 g, 80%).

Workup

  1. temperatureto reflux temperature
  2. filtrationfiltered through a pad of diatomaceous earth
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-79e238124caf40eeb6e3b32c260cb7fc
Source dataset
uspto-grants-2011_05
Patent number
US07947718B2

Reaction notes

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