HCID 20150397, compound → HCID 20150385, compound

HRID 568739Notes

Reaction equation

HRID 568739 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:29])=[C:5]([CH3:28])[C:6]2[O:11][C:10]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH2:17][CH2:16]3)([CH3:12])[CH2:9][CH2:8][C:7]=2[C:26]=1[CH3:27]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:29])=[C:5]([CH3:28])[C:6]2[O:11][C:10]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:17][CH2:16]3)([CH3:12])[CH2:9][CH2:8][C:7]=2[C:26]=1[CH3:27]

Participants

4

Reactant 1

HCID 20150397HCID 20150397, compound

Product 1

HCID 20150385HCID 20150385, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution composed of 2.0 g of the 3,4-dihydro-6-methoxy-2-[2-[4-(3-methyl-2-butenyl)piperazin-1-yl]ethyl]-2,5,7,8-tetramethyl-2H-benzopyran obtained by the process of Example 13, 0.1 g of 5% palladium on carbon and 50 ml of ethanol was stirred at room temperature for 48 hours. The reaction mixture was filtered to remove the palladium on carbon and low-boiling substances were distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 1.24 g of 1-[2-(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)ethyl]-4-isopentylpiperazine [Compound (34)] having the following physical characteristics.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the palladium on carbon and low-boiling substances
  3. distillationwere distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-abf84a16832f4947ab850b3532cc9da3
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Reaction notes

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