Sodium Iodide → HCID 21288002, compound

HRID 868362Notes

Reaction equation

HRID 868362 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH:10]([CH3:14])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrCCCC[N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:45]([C:47]([CH3:49])=O)[CH3:46]>>[C:15]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:46][CH2:45][CH2:47][CH2:49][C:28]34[CH:35]=[CH:34][CH:33]=[CH:32][CH:29]3[C:30]([NH:26][C:27]4=[O:36])=[O:31])[CH:10]([CH3:14])[CH2:9]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 21288000HCID 21288000, compound

Product 1

HCID 21288002HCID 21288002, compound

Procedure

A mixture of 10.0 g of 1-diphenylmethyl-3-methylpiperazine [cf. Can. Pharm. J., 95 (8), 256 (1962)], 10.6 g of N-(4-bromobutyl)phthalimide, 6.2 g of potassium carbonate, 8.4 g of sodium iodide, and 100 ml of methyl ethyl ketone is refluxed with stirring for 4 hours. The reaction mixture is concentrated, and 100 ml of water is added. The aqueous mixture is extracted with three 100-ml portions of chloroform. The combined extracts are dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel with chloroform to give 19.2 g of 2-[4-(4-diphenylmethyl-2-methyl-1-piperazinyl)butyl]phthalimide.

Workup

  1. temperatureis refluxed
  2. concentrationThe reaction mixture is concentrated
  3. addition100 ml of water is added
  4. extractionThe aqueous mixture is extracted with three 100-ml portions of chloroform
  5. dry with materialThe combined extracts are dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel with chloroform

Sources & evidence

ORD record
ord-fbe4b4426a1e41f5bbc7f1739d6d82bd
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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