Sodium Hydroxide → 1-(5-Fluoropyridin-2-YL)ethanamine

HRID 2167774Notes

Reaction equation

HRID 2167774 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([NH:12]C(=O)C)[CH3:11])=[N:8][CH:9]=1>>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([NH2:12])[CH3:11])=[N:8][CH:9]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 66735551Acetamide, N-[(1S)-1-(5-fluoro-2-pyridinyl)ethyl]-

Product 1

HCID 574158241-(5-Fluoropyridin-2-YL)ethanamineYield 80.3%

Conditions

Temperature
27.5 °C

Procedure

A mixture of 5N aqueous NaOH solution (5 mL) and N-(1-(5-fluoropyridin-2-yl)ethyl)acetamide (180 mg, 0.4 mmol) was heated under reflux conditions for 12-16 h. After completion of the reaction, the reaction mixture was cooled to a temperature of 20-35° C. The reaction mixture was extracted with DCM, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 45 mg of the title compound as a yellow liquid.

Workup

  1. temperaturewas heated under reflux conditions for 12-16 h
  2. customAfter completion of the reaction
  3. extractionThe reaction mixture was extracted with DCM
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c692cbd37654e0899e799f8b9e73310
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Reaction notes

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