Potassium Hydroxide → Amantadine

HRID 926901

Reaction equation

HRID 926901 reaction equation
Cl.[C:2]12([NH2:12])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[OH-].[K+]>>[C:2]12([NH2:12])[CH2:9][CH:8]3[CH2:7][CH:6]([CH2:5][CH:4]([CH2:10]3)[CH2:3]1)[CH2:11]2

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 64150Amantadine Hydrochloride

Product 1

HCID 2130Amantadine

Procedure

An aqueous solution of 1-adamantylamine hydrochloride (Alfa-Aesar, 99%) was treated with potassium hydroxide and extracted with toluene, dried over Na2SO4, filtered and stripped down by rotary evaporation to give 30.3 g 1-adamantylamine (200 mmol). The procedure for compound 1, above, was followed except the reaction was heated at 45° C. overnight yielding 26.23 g white solids (62.8 mmol, 63% yield). When performing the activated carbon treatment 2:1 water/absolute ethanol was used to dissolve the residue.

Workup

  1. extractionextracted with toluene
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customstripped down by rotary evaporation

Sources & evidence

ORD record
ord-2a96ff9932fe44e98afecd7913bfb30a
Source dataset
uspto-grants-2016_03
Patent number
US09289757B2

Linked notes

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