Toluene → 1-[2-(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)ethyl]-4-(2-hydroxyethyl)piperazine

HRID 568738Notes

Reaction equation

HRID 568738 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[CH3:10][O:11][C:12]1[C:13]([CH3:38])=[C:14]([CH3:37])[C:15]2[O:20][C:19]([CH2:22][CH2:23]OS(C3C=CC(C)=CC=3)(=O)=O)([CH3:21])[CH2:18][CH2:17][C:16]=2[C:35]=1[CH3:36].C1(C)C=CC=CC=1>O>[CH3:10][O:11][C:12]1[C:13]([CH3:38])=[C:14]([CH3:37])[C:15]2[O:20][C:19]([CH2:22][CH2:23][N:7]3[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]3)([CH3:21])[CH2:18][CH2:17][C:16]=2[C:35]=1[CH3:36]

Participants

5

Reactant 3

HCID 1140TolueneHCID 76771-(2-Hydroxyethyl)piperazineHCID 139094223,4-dihydro-6-methoxy-2-[2-(p-toluenesulfonyloxy)ethyl]-2,5,7,8-tetramethyl-2H-benzopyran

Product 1

HCID 143926471-[2-(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)ethyl]-4-(2-hydroxyethyl)piperazineYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution composed of 20 g of N-(2-hydroxyethyl)piperazine, 5 g of 3,4-dihydro-6-methoxy-2-[2-(p-toluenesulfonyloxy)ethyl]-2,5,7,8-tetramethyl-2H-benzopyran and 100 ml of toluene was refluxed for 8 hours in a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into water and extracted with diethyl ether. The extract was washed with water and dried over anhydrous sodium sulfate. Low-boiling substances were distilled off under reduced pressure and the residue was purified by silica gel column chromatography to give 3.66 g of 1-[2-(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)ethyl]-4-(2-hydroxyethyl)piperazine [Compound (35)] having the following physical characteristics.

Workup

  1. temperaturewas refluxed for 8 hours in a nitrogen atmosphere
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationwere distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-95ed2f7a1c6443619a465fa4562f040c
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Reaction notes

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