Dimethylamine → HCID 124494, compound

HRID 1440813Notes

Reaction equation

HRID 1440813 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.

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-493b9b25ab794153ae9ff155cdeb5be9
Source dataset
uspto-grants-1996_03
Patent number
US05500444

Reaction notes

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