Dimethylamine → n,n-dimethyl-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 2088738Notes

Reaction equation

HRID 2088738 reaction equation
CO.CN(C)C[CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1.[CH3:17][NH:18][CH3:19].C1C(=O)CC2C(=CC=CC=2)C1>O1CCCC1>[CH3:17][N:18]([CH3:19])[CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 887MethanolHCID 682662-TetraloneHCID 21063044HCID 21063044, compound

Product 1

HCID 242461n,n-dimethyl-1,2,3,4-tetrahydronaphthalen-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

46 ml of a methanol solution of 0.3 M sodium cyanoborohydride-1/2 zinc chloride and 6.9 mL of a tetrahydrofuran solution of 2 M dimethylamine were added to a tetrahydrofuran (10 mL) solution of 2.02 g of β-tetralone, and stirred for a day at room temperature. The reaction liquid was concentrated, and 1 N hydrochloric acid was added thereto. The acidic solution was washed with ethyl acetate, then made alkaline with aqueous 5 M sodium hydroxide solution, and extracted with ethyl acetate. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated away to obtain 857 mg of the entitled compound as a colorless oily substance.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated
  3. addition1 N hydrochloric acid was added
  4. washThe acidic solution was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThis was washed with saturated saline water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customthe solvent was evaporated away

Sources & evidence

ORD record
ord-6196f24260f544bb88b4ad4091c8b7d6
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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