Hydrochloric Acid → HCID 86635278, compound

HRID 1013515Notes

Reaction equation

HRID 1013515 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[CH:3][CH:2]=1.[ClH:15]>CO.[OH-].[OH-].[Pd+2]>[ClH:15].[NH:1]1[CH2:2][CH2:3][CH:4]([P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 3623756diethyl pyridin-4-ylphosphonate

Product 1

HCID 86635278HCID 86635278, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Diethyl pyridin-4-ylphosphonate (3.8 g, 17.66 mmol) and palladium hydroxide on carbon (1.240 g, 1.766 mmol) were taken up in MeOH (90 mL)/HCl (10 mL, 20.00 mmol). The suspension was agitated under H2 @ 40-50 psi for 7 days. The catalyst was removed by filtration and the filtrate concentrated in vacuo to give diethyl piperidin-4-ylphosphonate hydrochloride as a green gum. 1H NMR (DMSO-d6, 600 MHz) δ 9.26 (br s, 1H), 8.84 (br s, 1H), 3.96 (m, 4H), 3.20 (m, 2H), 2.80 (m, 2H), 2.10 (m, 1H), 1.84 (m, 2H), 1.68 (m, 2H), 1.19 (t, J=7.2 Hz, 6H). MS: cal'd 222 (MH+), exp 222 (MH+).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-3776f75d69e4483e8bbdc3c5bd12e788
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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