Hydrochloric Acid → 5-Aminomethyl-2-(1-hydroxy-3-methyl-butyl)-pyridine hydrochloride

HRID 911611Notes

Reaction equation

HRID 911611 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14])=[N:9][CH:10]=1)=[N+]=[N-].[ClH:17]>C(O)C.[Pd]>[ClH:17].[NH2:1][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([OH:16])[CH2:12][CH:13]([CH3:14])[CH3:15])=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 576563405-Azidomethyl-2-(3-methyl-butyryl)-pyridine

Product 1

HCID 667069535-Aminomethyl-2-(1-hydroxy-3-methyl-butyl)-pyridine hydrochlorideYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add 10% Pd/C (20 mg) to a solution of 5-azidomethyl-2-(3-methyl-butyryl)-pyridine (80 mg, 0.367 mmol) in ethanol (10 mL) containing concentrated HCl (1 mL). Submit the mixture to hydrogenation at atmospheric pressure for 2 h. Filter the reaction mixture over Celite® and concentrate in vacuo to afford the desired intermediate (95 mg, 98%). MS (ES+) m/z: 195 (M+H)+.

Workup

  1. customfor 2 h
  2. filtrationFilter the reaction mixture over Celite®
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-ea1a1b4f33f94d9db4d3c641f81fd9d7
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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