Methyl iodide → 3-Methoxy-1-adamantylamine

HRID 1045313

Reaction equation

HRID 1045313 reaction equation
[H-].[K+].[NH2:3][C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][C:6]([OH:14])([CH2:7]3)[CH2:5]1)[CH2:11]2.I[CH3:16]>O1CCCC1.C(Cl)Cl>[CH3:16][O:14][C:6]12[CH2:12][CH:10]3[CH2:9][CH:8]([CH2:13][C:4]([NH2:3])([CH2:11]3)[CH2:5]1)[CH2:7]2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 82127Potassium hydrideHCID 6586453-Amino-1-adamantanol

Product 1

HCID 221162623-Methoxy-1-adamantylamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, ice-water chilled suspension of potassium hydride (0.680 gm; 5.95 mmol) in 15.0 ml of tetrahydrofuran is added a mixture of 1-aminoadamantane-3-ol (1.00 g; 5.95 mmol) and 15.0 ml of tetrahydrofuran dropwise over 30 minutes. The resulting mixture is then stirred for an addition 30 minutes and iodomethane (0.370 ml; 5.95 mmol) is then added dropwise over one minute. The resulting opaque white reaction is then stirred at room temperature for 18 hours. The mixture is then diluted with 50 ml of methylene chloride and filtered to remove the inorganic impurities. The filtrate is then concentrated and purified on silica gel employing a SIMS/Biotage apparatus and 19% methanol and 1% ammonium hydroxide in methylene chloride as eluent to yield 3-methoxy-1-adamantylamine as an opaque oil.

Workup

  1. additionis added
  2. additionis then added dropwise over one minute
  3. customThe resulting opaque white reaction
  4. filtrationfiltered
  5. customto remove the inorganic impurities
  6. concentrationThe filtrate is then concentrated
  7. custompurified on silica gel employing a SIMS/Biotage apparatus and 19% methanol and 1% ammonium hydroxide in methylene chloride as eluent

Sources & evidence

ORD record
ord-4eb25845d1d74710956f4f46b1af3f0a
Source dataset
uspto-grants-2013_10
Patent number
US08569250B2

Linked notes

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