1,3-Benzodioxole-5-carbonyl chloride → HCID 18914204, compound

HRID 1292107Notes

Reaction equation

HRID 1292107 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][O:7][C:8]2[CH:24]=[CH:23][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][OH:22])[CH2:16][CH2:15]3)=[O:13])=[CH:10][C:9]=2[CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:4][CH:3]=1.[C:31](Cl)(=[O:41])[C:32]1[CH:40]=[CH:39][C:38]2[O:37][CH2:36][O:35][C:34]=2[CH:33]=1>ClCCl.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:24]=[CH:23][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:31](=[O:41])[C:32]4[CH:40]=[CH:39][C:38]5[O:37][CH2:36][O:35][C:34]=5[CH:33]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:10][C:9]=2[CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 18914234HCID 18914234, compound

Product 1

HCID 18914204HCID 18914204, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-[4-(4-fluorobenzyloxy)-3-isobutylbenzoyl]-4-(2-hydroxyethyl) piperazine (1.95 g) was dissolved in a mixture of dichloromethane (30 ml) and triethylamine (1.04 ml) and then, while being cooled with ice, piperonyloyl chloride (0.93 g) was added thereto dropwise. After being stirred for 12 hours at room temperature, the reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine successively, dried over sodium sulfate anhydride, and then concentrated under a vacuum. Thus obtained residue was purified by silica gel column chromatography (chloroform:methanol=50:1), thereby yielding 1.92 g of the aimed compound.

Workup

  1. additionwas added
  2. washthe reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine successively
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationconcentrated under a vacuum
  5. customThus obtained residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-c8c83c5358d14072b0958878f7cbf9f6
Source dataset
uspto-grants-1998_05
Patent number
US05756505

Reaction notes

Loading…