Iodoethane → HCID 20066619, compound

HRID 358767Notes

Reaction equation

HRID 358767 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:10][CH:9]1[CH2:28][OH:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:32](I)[CH3:33]>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)[CH2:10][CH:9]1[CH2:28][O:29][CH2:32][CH3:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 20066652HCID 20066652, compound

Product 1

HCID 20066619HCID 20066619, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In N,N-dimethylformamide (2 ml) is dissolved 1-benzyl-4-(3,4,5-trimethoxybenzoyl)piperazine-2-methanol (1.0 g). The solution is added dropwise to a mixture of sodium hydride (0.15 g) and N,N-dimethylformamide (4 ml) taking 5 minutes at 0 ° C while stirring. To the mixture is further added ethyl iodide (0.5 g) at 0° C., followed by stirring for 30 minutes at room temperature. The reaction mixture is poured into icewater and extracted with ethyl acetate. The organic layer is washed with water and dried, then the solvent is distilled off under reduced pressure to afford 1-benzyl-2-ethoxymethyl-4-(3,4,5trimethoxybenzoyl)piperazine as a colorless oily product (1.0 g). This product is led to its hydrochloride, followed by recrystallization from acetone to give colorless needles, m.p. 130-132° C.

Workup

  1. customat 0° C.
  2. stirringby stirring for 30 minutes at room temperature
  3. additionThe reaction mixture is poured into icewater
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with water
  6. customdried
  7. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-fbd90e2011bb4ad2868d9709bca2f414
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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