Hydrochloric Acid → alpha,alpha-Dimethyl-2-naphthaleneethanamine

HRID 895873Notes

Reaction equation

HRID 895873 reaction equation
[CH3:1][C:2]([NH:15]C(=O)C)([CH3:14])[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.Cl.[OH-].[Na+]>O>[CH3:14][C:2]([NH2:15])([CH3:1])[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22382419N-[2-Methyl-1-(naphthalen-2-yl)propan-2-yl]acetamide

Product 1

HCID 15369616alpha,alpha-Dimethyl-2-naphthaleneethanamineYield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To N-[2-methyl-1-(naphthalen-2-yl)propan-2-yl]acetamide (26 mg) obtained in Step 8 was added 6N hydrochloric acid (2 ml) and the mixture was heated under reflux for 5 hr. The reaction mixture was poured into water, made basic with a 4N aqueous sodium hydroxide solution, and extracted with diethyl ether. The organic layer was washed with water, dried over potassium carbonate and concentrated under reduced pressure to give the title compound (19 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hr
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over potassium carbonate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d1a65d1e9f44f4cb61297243c0c3a2c
Source dataset
uspto-grants-2005_07
Patent number
US06916956B2

Reaction notes

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