Sulfuric Acid → 4-Aminoadamantan-1-ol

HRID 234736Notes

Reaction equation

HRID 234736 reaction equation
S(=O)(=O)(O)O.Cl.[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[NH2:17])[CH2:14]2.[OH-:18].[Na+]>[N+]([O-])(O)=O>[OH:18][C:13]12[CH2:15][CH:9]3[CH2:10][CH:11]([CH2:16][CH:7]([CH:8]3[NH2:17])[CH2:14]1)[CH2:12]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 253312-Aminoadamantane hydrochloride

Product 1

HCID 28574474-Aminoadamantan-1-ol

Reagents, catalysts & solvents 1

HCID 944Nitric AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a mixture of concentrated sulfuric acid (300 ml) and concentrated nitric acid (30 ml) cooled in an ice bath to 10° C. is added tricyclo[3.3.1.13,7 ]decan-2-amine hydrochloride (20 g; 0.107 mole) in 5 g portions over 10 minutes. This mixture is then stirred for 2 hours with cooling. The reaction mixture is poured over ice and the pH raised to pH 10-11 using 40% NaOH. This mixture is extracted with chloroform, dried over MgSO4 and evaporated to dryness to give 5-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine as a solid residue (m.p. 267°-270° C.) which is used directly in step B.

Workup

  1. temperaturewith cooling
  2. additionThe reaction mixture is poured over ice
  3. temperaturethe pH raised to pH 10-11
  4. extractionThis mixture is extracted with chloroform
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-c0886ad161f949e781dbe9b11af38c47
Source dataset
uspto-grants-1997_01
Patent number
US05596020

Reaction notes

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