Sodium Hydroxide → 3-[5-(3-Aminopropyl)pyridin-2-yl]propylamine

HRID 49577Notes

Reaction equation

HRID 49577 reaction equation
C([NH:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][NH:17]C(=O)C)=[N:12][CH:13]=1)(=O)C.[OH-].[Na+]>Cl>[NH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][NH2:17])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11173477N-(3-{5-[3-(Acetylamino)propyl]pyridin-2-yl}propyl)acetamide

Product 1

HCID 98130173-[5-(3-Aminopropyl)pyridin-2-yl]propylamineYield 191.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(3-{5-[3-(acetylamino)propyl]pyridin-2-yl}propyl)acetamide (9-1) (1.5 g) in 3N HCl (15 mL) was heated under reflux for 3 hours. At room temperature, 5N NaOH (about 10 mL) was added to the solution until a pH of about 10 was achieved. The solution was extracted three times with sec-butyl alcohol (15 mL). The extracts were combined and concentrated under reduced pressure to give 12-1 (2 g). The melting point and NMR spectra were identical to those observed for 12-1 in Example 13.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionThe solution was extracted three times with sec-butyl alcohol (15 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-834d4ecac4e145d780ad1dc831fab356
Source dataset
uspto-grants-2004_03
Patent number
US06706885B2

Reaction notes

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