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

HRID 551584Notes

Reaction equation

HRID 551584 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClCCCOC1C=CC(CN2CCCCC2)=NC=1.N1CCCCC1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CCC>[NH3:1].[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)=[CH:10][N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 10340Sodium CarbonateHCID 111745632-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridineHCID 67188055HCID 67188055, compound

Product 2

HCID 222AmmoniaYield 3%HCID 111745632-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridineYield 10%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-Piperidin-1-ylmethyl-5-(3-piperidin-1-yl-propoxy)-pyridine. A solution of 5-(3-chloro-propoxy)-2-piperidin-1-ylmethyl-pyridine (0.25 g, 0.86 mmol), piperidine (0.09 mL, 0.94 mmol), KI (0.003 g, 0.017 mmol), and Na2CO3 (0.045 g, 0.43 mmol) in 1-butanol (5 mL) was heated to 95° C. After 18 h the reaction mixture was concentrated, diluted with DCM (50 mL) and filtered through a pad of diatomaceous earth. The filtrate was concentrated and chromatography of the residue (SiO2: 3-8% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.025 g, 10%). MS (ESI): exact mass calcd. for C19H31N3O, 317.3; m/z found, 318.5. 1H NMR (400 MHz, CDCl3): 8.23 (d, J=2.8, 1H), 7.29 (d, J=8.1, 1H), 7.16 (dd, J=8.6, 3.0, 1H), 4.03 (t, J=6.3, 2H), 3.55 (s, 2H), 2.48-2.40 (m, 10H), 2.01-1.96 (m, 2H), 1.61-1.46 (m, 8H), 1.43 (br s, 4H).

Workup

  1. concentrationAfter 18 h the reaction mixture was concentrated
  2. additiondiluted with DCM (50 mL)
  3. filtrationfiltered through a pad of diatomaceous earth
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-14175054d084496b919d8a8b1cee18e3
Source dataset
uspto-grants-2011_05
Patent number
US07947718B2

Reaction notes

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