Hexane → HCID 86743747, compound

HRID 1199402Notes

Reaction equation

HRID 1199402 reaction equation
[Li]CCCC.CCCCCC.[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]1.Br[CH2:24][CH2:25][CH:26]1[O:30][CH2:29][CH2:28][O:27]1>O1CCCC1.O.C(Cl)Cl>[CH3:12][N:13]1[CH2:14][CH2:15][N:16]([S:19]([CH2:22][CH2:24][CH2:25][CH:26]2[O:30][CH2:29][CH2:28][O:27]2)(=[O:21])=[O:20])[CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 8177701-(Methanesulfonyl)-4-methylpiperazineHCID 178418339Butyllithium

Product 1

HCID 86743747HCID 86743747, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21908982Water methylene chlorideSolvent

Procedure

At 0° to 5° C., 87.5 ml of 1.6 molar BuLi solution in hexan (0.14 mol) are added dropwise to 23 g (0.13 mol) of methanesulphonic acid-N'-methylpiperazide dissolved in 200 ml of anhydrous tetrahydrofuran, the resulting suspension is stirred for 90 minutes at ambient temperature and then 23.4 g of 2-(2-bromoethyl)-1,3-dioxolan (0.13 mol) in 200 ml of anhydrous tetrahydrofuran are added dropwise, forming a clear solution. After 5 hours' stirring the solvent is eliminated, the residue is taken up with water/methylene chloride and the aqueous phase is extracted several times with methylene chloride. The methylene chloride solution is dried and the solvent is drawn off. The oil residue is filtered over a column of silica gel using methylene chloride/methanol 9:1 as eluant. After the solvent has been driven off again, 20.7 of the desired compound are obtained as a light coloured oil.

Workup

  1. customforming a clear solution
  2. stirringAfter 5 hours' stirring the solvent
  3. extractionthe aqueous phase is extracted several times with methylene chloride
  4. dry with materialThe methylene chloride solution is dried
  5. filtrationThe oil residue is filtered over a column of silica gel

Sources & evidence

ORD record
ord-18eef209c0ca45a580543d3297ccb963
Source dataset
uspto-grants-1990_02
Patent number
US04900729

Reaction notes

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