Hydrochloric Acid → HCID 16100374, compound

HRID 1424580Notes

Reaction equation

HRID 1424580 reaction equation
[OH:1][C:2]12[CH2:12][CH:6]3[CH2:7][C:8]([OH:11])([CH2:10][CH:4]([CH:5]3[NH:13]C(=O)C)[CH2:3]1)[CH2:9]2.Cl>>[NH2:13][CH:5]1[CH:4]2[CH2:3][C:2]3([OH:1])[CH2:9][C:8]([OH:11])([CH2:7][CH:6]1[CH2:12]3)[CH2:10]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 16100373HCID 16100373, compound

Product 1

HCID 16100374HCID 16100374, compoundYield 56%

Conditions

Temperature
80 °C

Procedure

To N-(5,7-dihydroxy-2-adamantyl)acetamide (110 mg, 0.489 mmol) was added 4N aq HCl (3 mL) slowly. The reaction mixture was heated to 80° C. overnight. The mixture was cooled to rt and concentrated. The residue was treated with satd aq NaHCO3. The water was removed under reduced pressure, and the solid was triturated with methanol. The mixture was filtered, and the solids were washed with methanol. The filtrate was concentrated give to 6-aminoadamantane-1,3-diol (50 mg, 56%). 1H-NMR (400 MHz, D2O): δ=1.45 (m, 2H), 1.63 (m, 6H), 1.73 (m, 4H), 2.12 (m, 2H), 3.27 (m, 1H).

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated
  3. additionThe residue was treated with satd aq NaHCO3
  4. customThe water was removed under reduced pressure
  5. customthe solid was triturated with methanol
  6. filtrationThe mixture was filtered
  7. washthe solids were washed with methanol
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-cf6a6732f8704a039012786dd76c3cee
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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