Potassium Iodide → 1-[2-(1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)ethyl]-4-[3,3-bis (4-fluorophenyl)propyl]piperazine (E)-2-butenedioate

HRID 275394Notes

Reaction equation

HRID 275394 reaction equation
Cl[CH2:2][CH2:3][C:4]1([CH2:18][CH3:19])[C:9]2[CH:10]=[C:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][CH2:6][O:5]1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:23][CH:22]=1.[C:43](=[O:46])([O-:45])[O-].[K+].[K+].[I-].[K+].CN(C)C=[O:54]>O>[C:12]([OH:14])(=[O:54])/[CH:13]=[CH:8]/[C:43]([OH:45])=[O:46].[CH2:18]([C:4]1([CH2:3][CH2:2][N:33]2[CH2:32][CH2:31][N:30]([CH2:29][CH2:28][CH:27]([C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)[C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=3)[CH2:35][CH2:34]2)[C:9]2[CH:10]=[C:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][CH2:6][O:5]1)[CH3:19]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 138832821-[3,3-Bis(4-fluorophenyl)propyl]piperazineHCID 200879571-(2-chloroethyl)-1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran

Product 1

HCID 677847001-[2-(1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)ethyl]-4-[3,3-bis (4-fluorophenyl)propyl]piperazine (E)-2-butenedioateYield 61.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.6 of 1-(2-chloroethyl)-1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran, 8 g of 1-[3,3-bis(4-fluorophenyl)propyl]piperazine, 5.2 g of potassium carbonate and 0.4 g of potassium iodide in 100 ml of dimethylformamide was refluxed for 4 h. Water was added and the base was extracted twice with ethyl acetate. After washing, drying and evaporation the difumarate was prepared in absolute ethanol to yield 13.2 g (61.2%) of 1-[2-(1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)ethyl]-4-[3,3-bis (4-fluorophenyl)propyl]piperazine (E)-2-butenedioate (1:2) salt.

Workup

  1. temperaturewas refluxed for 4 h
  2. extractionthe base was extracted twice with ethyl acetate
  3. washAfter washing
  4. customdrying
  5. customevaporation the difumarate
  6. customwas prepared in absolute ethanol

Sources & evidence

ORD record
ord-e68fe048c1cd43df89038a03ebcfdbd0
Source dataset
uspto-grants-1995_02
Patent number
US05393759

Reaction notes

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