Diisopropylethylamine → HCID 54423605, compound

HRID 2267961Notes

Reaction equation

HRID 2267961 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][CH2:12]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:17][CH:16]=1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>CS(C)=O.[I-].[Na+]>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][CH2:12][N:25]2[CH2:24][CH2:23][N:22]([CH:21]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:18]3[CH:17]=[CH:16][C:15]([F:14])=[CH:20][CH:19]=3)[CH2:27][CH2:26]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 516892Sodium BicarbonateHCID 54330420HCID 54330420, compound

Product 1

HCID 54423605HCID 54423605, compound

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
65 °C

Procedure

A solution of 0.5 gram (0.002 mole) of 3-(4-nitrophenyl)-2-propenyl chloride in 5 mL of dimethyl sulfoxide was added to a solution of 0.7 gram (0.002 mole) of N-[bis(4-fluorophenyl)methyl]piperazine in 10 mL of dimethyl sulfoxide. To this was added 0.1 gram (0.0005 mole) of sodium iodide as a catalyst. Upon completion of the addition 1.2 grams (0.010 mole) of N,N-diisopropylethylamine was added dropwise. To effect solution the reaction mixture was then warmed to 50-80° C., where it stirred for four hours . After this time the reaction mixture was cooled to ambient temperature, where it stirred for about 18 hours. The reaction mixture was then poured into 50 mL of aqueous saturated sodium bicarbonate solution and then extracted with three 50 mL portions of diethyl ether. The combined extracts were washed with 75 mL of aqueous saturated sodium chloride solution, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding a crude oil, which was subjected to column chromatography on silica gel. Elution was accomplished with 1:1 ethyl acetate:heptane. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.5 gram of of N-[3-(4-nitrophenyl)-2-propenyl]-N′-[bis(4-fluorophenyl)methyl]piperazine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwas added dropwise
  2. temperatureAfter this time the reaction mixture was cooled to ambient temperature
  3. stirringwhere it stirred for about 18 hours
  4. extractionextracted with three 50 mL portions of diethyl ether
  5. washThe combined extracts were washed with 75 mL of aqueous saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customyielding a crude oil, which
  10. washElution
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a6ad55383104b1794b1c71caf0c42ec
Source dataset
uspto-grants-2001_12
Patent number
USH0002007H1

Reaction notes

Loading…