Dimethylamine → HCID 124494, compound

HRID 846173Notes

Reaction equation

HRID 846173 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:21])=[C:7]([CH3:20])[C:8]2[O:13][C:12]([CH2:15][CH2:16]Br)([CH3:14])[CH2:11][CH2:10][C:9]=2[C:18]=1[CH3:19])(=[O:3])[CH3:2].[CH3:22][NH:23][CH3:24].O>CN(C)C=O>[C:1]([O:4][C:5]1[C:6]([CH3:21])=[C:7]([CH3:20])[C:8]2[O:13][C:12]([CH2:15][CH2:16][N:23]([CH3:24])[CH3:22])([CH3:14])[CH2:11][CH2:10][C:9]=2[C:18]=1[CH3:19])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 14776643HCID 14776643, compound

Product 1

HCID 124494HCID 124494, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.55 g (0.01 mol) of 3,4-dihydro-2-(2- bromoethyl)-2,5,7,8-tetramethyl-2H-benzopyran-6-yl acetate and 2.0 g of liquid dimethylamine in 50 ml of dimethylformamide is stirred at room temperature for 40 hours. Water is added and the product is extracted with ethyl acetate and ethyl ether. The extract is washed with water, dried over anhydrous sodium sulfate, filtered and evaporated. The resulting oil crystallizes from a mixture of ethyl ether and pentane to give 2.05 g of 3,4-dihydro-2-(2-dimethylaminoethyl)-2,5,7,8-tetramethyl-2H-benzopyran-6-yl acetate as the free base. The hydrochloride salt prepared by standard methods and recrystallized from isopropanol has m.p. 263°-270° C.

Workup

  1. extractionthe product is extracted with ethyl acetate and ethyl ether
  2. washThe extract is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oil crystallizes from a mixture of ethyl ether and pentane

Sources & evidence

ORD record
ord-665a8b4e72734cf99ff3349028eff3c8
Source dataset
uspto-grants-1992_08
Patent number
US05135945

Reaction notes

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