Nitric Acid → 3-Amino-1-adamantanol

HRID 234742

Reaction equation

HRID 234742 reaction equation
[N+]([O-])(O)=O.Cl.[C:6]12([NH2:16])[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.[OH-:17].[Na+]>S(=O)(=O)(O)O>[OH:17][C:8]12[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][C:6]([NH2:16])([CH2:15]3)[CH2:7]1)[CH2:14]2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 64150Amantadine Hydrochloride

Product 1

HCID 6586453-Amino-1-adamantanol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a mixture of 150 ml of concentrated sulfuric acid and 15 ml of concentrated nitric acid, cooled to 10° C. is added 10 g (0.053 moles) of 1-adamantanamine hydrochloride over 5 minutes. This mixture is stirred in an ice bath for 4 hours. The reaction is then poured over ice and the pH adjusted to pH 10 using 50% NaOH. The product is extracted into chloroform which is dried over MgSO4 and then evaporated to dryness. The residue is recrystallized from ethyl acetate to give 3-hydroxytricyclo[3.3.1.13,7 ]decan-1-amine (m.p. 260°-264° C.) which is used directly in step B.

Workup

  1. additionThe reaction is then poured over ice
  2. extractionThe product is extracted into chloroform which
  3. dry with materialis dried over MgSO4
  4. customevaporated to dryness
  5. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6e7885fc1cc547e48924216fe5c21fea
Source dataset
uspto-grants-1997_01
Patent number
US05596020

Linked notes

Loading…