Methyl iodide → 6-Methoxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxin

HRID 37179

Reaction equation

HRID 37179 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:36]=[CH:35][C:7]2[O:8][C:9]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH:20]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:10][O:11][C:6]=2[CH:5]=1.[CH3:37]I>CN(C)C=O>[CH3:37][O:3][C:4]1[CH:36]=[CH:35][C:7]2[O:8][C:9]([C:12]([N:14]3[CH2:15][CH2:16][N:17]([CH:20]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)[CH2:18][CH2:19]3)=[O:13])=[CH:10][O:11][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 98044716-Hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxin

Product 1

HCID 110272136-Methoxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxinYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 0.98 mmol of 60% sodium hydride suspended in oil to a solution of 0.82 mmol of 6-hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxin in 10 cm3 of N,N-dimethylformamide under a nitrogen atmosphere. Stir for 15 minutes at room temperature, then add dropwise 0.98 mmol of methyl iodide. Stir for 2 hours at room temperature and then concentrate to dryness under reduced pressure and purify the resulting crude product by chromatography on a silica column (eluant:petroleum ether/ethyl acetate, 50:50). 6-Methoxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxin is thereby obtained in a yield of 83%.

Workup

  1. stirringStir for 2 hours at room temperature
  2. concentrationconcentrate to dryness under reduced pressure
  3. custompurify the resulting crude product by chromatography on a silica column (eluant:petroleum ether/ethyl acetate, 50:50)

Sources & evidence

ORD record
ord-1d2220bda5e84a3dbfd342792eb53448
Source dataset
uspto-grants-1995_05
Patent number
US05420132

Linked notes

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