Iodoethane → HCID 18753337, compound

HRID 1838232Notes

Reaction equation

HRID 1838232 reaction equation
[CH:1](NC(C)C)(C)[CH3:2].C([Li])CCC.CCCCCC.[CH2:19]([N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[C:34]([C:40]([F:43])([F:42])[F:41])[CH:33]=2)[CH2:28][C:27]1=[O:44])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(I)C.[Cl-].[NH4+]>C1COCC1>[CH2:19]([N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[C:34]([C:40]([F:42])([F:43])[F:41])[CH:33]=2)[CH:28]([CH2:1][CH3:2])[C:27]1=[O:44])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 6340IodoethaneHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 18753364HCID 18753364, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 18753337HCID 18753337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A 0.94 ml portion of diisopropylamine was dissolved in 10 ml of anhydrous THF, and the solution was mixed with 4.5 ml of 1.47 M butyl lithium/hexane solution at −20° C., stirred for 10 minutes and then cooled to −78° C. A 20 ml portion of anhydrous THF solution containing 2 g of 4-(4-benzyl-3-oxopiperazin-1-yl)-2-trifluoromethylbenzonitrile synthesized in Reference Example 1-15 was added dropwise thereto, and the mixture was stirred for 20 minutes and then mixed with 0.67 ml of ethyl iodide. After warming up to −10° C., the reaction solution was poured into saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic layer was washed and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by a silica gel column chromatography, and 1.5 g of the title compound was obtained from hexane-ethyl acetate (1:1, v/v) eluate as a white foamy substance.

Workup

  1. customsynthesized in Reference Example 1-15
  2. additionwas added dropwise
  3. stirringthe mixture was stirred for 20 minutes
  4. temperatureAfter warming up to −10° C.
  5. extractionextracted with ethyl acetate
  6. washthe organic layer was washed
  7. customdried
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-69d5bd4b055949e5baaa400454d857c4
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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