Potassium Iodide → HCID 86747157, compound

HRID 275389Notes

Reaction equation

HRID 275389 reaction equation
Cl[CH2:2][CH2:3][C:4]1([CH2:16][CH3:17])[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][CH2:6][O:5]1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[CH2:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:21][CH:20]=1.[I-].[K+].[C:44](=[O:47])([O-:46])[O-].[K+].[K+].CN(C)C=[O:53]>>[C:12]([OH:14])(=[O:53])/[CH:13]=[CH:8]\[C:44]([OH:46])=[O:47].[CH2:16]([C:4]1([CH2:3][CH2:2][N:32]2[CH2:31][CH2:30][N:29]([CH2:28][CH2:27][CH2:26][CH:25]([C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[C:22]3[CH:21]=[CH:20][C:19]([F:18])=[CH:24][CH:23]=3)[CH2:34][CH2:33]2)[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][CH2:6][O:5]1)[CH3:17]

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 797291-(4,4-Bis(4-fluorophenyl)butyl)piperazineHCID 20087933HCID 20087933, compound

Product 1

HCID 86747157HCID 86747157, compound

Procedure

A mixture of 7.6 g of known 1-(2-chloroethyl)-1-ethyl-3,4-dihydro-6-methoxy-1H-2-benzopyran, 9 g of 1-[4,4-bis(4-fluorophenyl)butyl]piperazine, 0.4 g of potassium iodide, and 5 g of potassium carbonate in 100 ml of dimethylformamide was refluxed for 6 h. After hydrolysis the mixture was extracted with dimethyl ether, and the ethereal phase was washed, dried, and evaporated. The base was precipitated and the dimaleate salt was prepared in ethanol and recrystallized from ethanol-water (3:1) to give 13.8 g of 1-[2-(1-ethyl-3,4-dihydro-6-methoxy-1H-2-benzopyran-1-yl)ethyl]-4-[4,4-bis(4-fluorophenyl)butyl]piperazine (Z)-2-butenedioate (1:2) salt. mp 184° C.

Workup

  1. temperaturewas refluxed for 6 h
  2. customAfter hydrolysis the mixture
  3. extractionwas extracted with dimethyl ether
  4. washthe ethereal phase was washed
  5. customdried
  6. customevaporated
  7. customThe base was precipitated
  8. customrecrystallized from ethanol-water (3:1)

Sources & evidence

ORD record
ord-6e921437436e489baa5b3b90e2506772
Source dataset
uspto-grants-1995_02
Patent number
US05393759

Reaction notes

Loading…