Hydrochloric Acid → HCID 58933540, compound

HRID 854297Notes

Reaction equation

HRID 854297 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([CH:27](OCC)[O:28]CC)[CH:22]=2)=[O:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([CH:27]=[O:28])[CH:22]=2)=[O:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 58933634HCID 58933634, compound

Product 1

HCID 58933540HCID 58933540, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-{[(2-diethoxymethyl-pyridine-4-carbonyl)-amino]-methyl}-piperidine-1-carboxylic acid benzyl ester (1.3 g, 0.0029 mol) in dioxane (20 mL) was added 1N hydrochloric acid (40 mL) and the mixture was warmed to 50° C. for 1.5 h. The reaction was cooled, diluted with ethyl acetate (100 mL) and 10% aqueous sodium bicarbonate (100 mL), and stirred well. The organic layer was removed, dried over sodium sulfate, filtered and concentrated in vacuo to give 4-{[(2-formyl-pyridine-4-carbonyl)-amino]-methyl}-piperidine-1-carboxylic acid benzyl ester as an oil.

Workup

  1. temperatureThe reaction was cooled
  2. customThe organic layer was removed
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-951d25c75f48457ca02831be3f34e076
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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