Hydrochloric Acid → 6-[(Dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amine

HRID 854024Notes

Reaction equation

HRID 854024 reaction equation
Cl.C([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:10][CH2:9]2)(=O)C.Cl.[OH-].[Na+]>>[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:10][CH2:9]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 229985926-Acetylamino-2-(N,N-dimethylamino)methyltetralin hydrochloride

Product 1

HCID 219397216-[(Dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amineYield 36.4%

Procedure

6-Acetylamino-2-(N,N-dimethylamino)methyltetralin hydrochloride (0.879 g; obtained in Reference Example 31) was added to 2 N hydrochloric acid. The reaction mixture was heated under reflux for 90 minutes, and then an aqueous solution of 1 N sodium hydroxide was added thereto to thereby make the resulting mixture have pH of 9. Then, this was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated. The residue was purified by alumina column chromatography (eluent:ethyl acetate/hexane=1/1) to obtain the entitled compound (0.231 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 90 minutes
  3. extractionThen, this was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, then dried
  6. concentrationconcentrated
  7. customThe residue was purified by alumina column chromatography (eluent:ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-3a8d303674a74ed4aab14e68c5a9c698
Source dataset
uspto-grants-2007_08
Patent number
US07256204B2

Reaction notes

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