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

HRID 30461Notes

Reaction equation

HRID 30461 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.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CCC>[NH3:10].[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 3

HCID 8082PiperidineHCID 10340Sodium CarbonateHCID 67188055HCID 67188055, compound

Product 2

HCID 222AmmoniaYield 3%HCID 111745632-Piperdin-1-ylmethyl-5-(3-piperdin-1-yl-propoxy)-pyridineYield 18.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-(3-chloro-propoxy)-2-piperidin-1ylmethyl-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-c7a7f232471840978fecac5f273717c2
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Reaction notes

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