Hydrochloric Acid → 3,4-Dihydro-2-(2-dimethylaminoethyl)-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol

HRID 1440815Notes

Reaction equation

HRID 1440815 reaction equation
Br[CH2:2][CH2:3][C:4]1([CH3:18])[CH2:9][CH2:8][C:7]2[C:10]([CH3:17])=[C:11]([OH:16])[C:12]([CH3:15])=[C:13]([CH3:14])[C:6]=2[O:5]1.[CH3:19][NH:20][CH3:21].O.[ClH:23]>CN(C)C=O.C(O)(C)C>[ClH:23].[CH3:19][N:20]([CH3:21])[CH2:2][CH2:3][C:4]1([CH3:18])[CH2:9][CH2:8][C:7]2[C:10]([CH3:17])=[C:11]([OH:16])[C:12]([CH3:15])=[C:13]([CH3:14])[C:6]=2[O:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 962WaterHCID 133751842-(2-Bromoethyl)-2,5,7,8-tetramethylchroman-6-ol

Product 1

HCID 1312423,4-Dihydro-2-(2-dimethylaminoethyl)-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 12.53 g of 3,4-dihydro-2-(2-bromoethyl)-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol and liquid gaseous dimethylamine in 50 ml of dimethylformamide is stirred at room temperature for 16 hours. Water is added and the product is extracted with ethyl ether. The extract is washed with water, dried over anhydrous sodium sulfate, filtered and evaporated. One equivalent of hydrochloride acid in isopropanol is added and the resulting precipitate is recrystallized twice from isopropanol/water to yield 9.44 g of the title compound, mp 300° C.

Workup

  1. extractionthe product is extracted with ethyl ether
  2. washThe extract is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customthe resulting precipitate is recrystallized twice from isopropanol/water

Sources & evidence

ORD record
ord-55f5b95edc894b7bacedb41662a85137
Source dataset
uspto-grants-1996_03
Patent number
US05500444

Reaction notes

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