Dimethylformamide → HCID 86747156, compound

HRID 2255134Notes

Reaction equation

HRID 2255134 reaction equation
Cl.Cl.[CH2:3]([C:5]1([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:10]2[CH:11]=[C:12]([O:17][CH3:18])[C:13]([O:15][CH3:16])=[CH:14][C:9]=2[CH2:8][CH2:7][O:6]1)[CH3:4].[F:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]([C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)[CH2:35][CH2:36][CH2:37]Cl)=[CH:30][CH:29]=1.[C:46](=[O:49])([O-:48])[O-].[K+].[K+].[I-].CN(C)C=[O:56]>>[C:13]([OH:15])(=[O:56])/[CH:14]=[CH:9]\[C:46]([OH:48])=[O:49].[CH2:3]([C:5]1([CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][N:24]([CH2:37][CH2:36][CH2:35][CH:34]([C:31]3[CH:30]=[CH:29][C:28]([F:27])=[CH:33][CH:32]=3)[C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[CH2:25][CH2:26]2)[C:10]2[CH:11]=[C:12]([O:17][CH3:18])[C:13]([O:15][CH3:16])=[CH:14][C:9]=2[CH2:8][CH2:7][O:6]1)[CH3:4]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 20087949HCID 20087949, compound

Product 1

HCID 86747156HCID 86747156, compoundYield 54%

Conditions

Temperature
100 °C

Procedure

A mixture of 6,2 g of crude 1-[2-(1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)ethyl]piperazine dihydrochloride, 6,8 g of 1,1-bis(4-fluorophenyl)-4-chlorobutane, 6,6 g of potassium carbonate and 2,9 g of potassiun iodide in 200 ml of dimethylformamide was heated at 100° C. for 2 h. After hydrolysis the mixture was extracted with a mixture of diethyl ether and ethyl acetate. After drying and evaporation the dimaleate was prepared in absolute ethanol to give 8 g (54,8%) of 1-[2-(1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)ethyl]-4-[4,4-bis(4-fluorophenyl)butyl]-piperazine (Z)-2-butenedioate (1:2) salt. mp 175° C.

Workup

  1. customAfter hydrolysis the mixture
  2. extractionwas extracted with a mixture of diethyl ether and ethyl acetate
  3. customAfter drying
  4. customevaporation the dimaleate
  5. customwas prepared in absolute ethanol

Sources & evidence

ORD record
ord-e8aaa225a6db493da6ff07c5e840ada5
Source dataset
uspto-grants-1993_08
Patent number
US05238939

Reaction notes

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