Pyridine → N-(6-Methoxy-2-tetralinyl)methylacetamide

HRID 854021Notes

Reaction equation

HRID 854021 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.Cl.[NH2:12][CH2:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=2)[CH2:15]1>C(OCC)(=O)C>[CH3:25][O:24][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[CH2:15][CH:14]([CH2:13][NH:12][C:1](=[O:3])[CH3:2])[CH2:23][CH2:22]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 229985822-Aminomethyl-6-methoxytetralin hydrochloride

Product 1

HCID 22998632N-(6-Methoxy-2-tetralinyl)methylacetamideYield 62.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetyl chloride (0.67 g) was added to a pyridine solution (15 ml) of 2-aminomethyl-6-methoxytetralin hydrochloride (1.5 g; obtained in Reference Example 11), and the reaction mixture was stirred at room temperature for 16 hours, to which was added ethyl acetate. The organic layer was washed with 1 N hydrochloric acid and a saturated aqueous sodium bicarbonate solution, then dried, and concentrated. The resulting crude crystals were recrystallized from ethyl acetate-diisopropyl ether to obtain the entitled compound (960 mg).

Workup

  1. washThe organic layer was washed with 1 N hydrochloric acid
  2. dry with materiala saturated aqueous sodium bicarbonate solution, then dried
  3. concentrationconcentrated
  4. customThe resulting crude crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-a82c6333f9f942a0adfb5f70c94f360a
Source dataset
uspto-grants-2007_08
Patent number
US07256204B2

Reaction notes

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