Methanesulfonyl chloride → HCID 19701055, compound

HRID 861915Notes

Reaction equation

HRID 861915 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)O)=[CH:5][CH:4]=1.CS(Cl)(=O)=O.[CH:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25].C(=O)(O)[O-].[Na+]>ClCCl.C(N(CC)CC)C>[CH:24]([N:26]1[CH2:31][CH2:30][N:29]([CH:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:28][CH2:27]1)=[O:25]

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 69768p,p'-Dimethoxybenzhydryl alcoholHCID 821911-PiperazinecarboxaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 19701055HCID 19701055, compoundYield 105.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-5 °C

Procedure

1.22 g of the above-mentioned compound (1) and 1.01 g of triethylamine were dissolved in 15 ml of dichloromethane. 5 ml of a dichloromethane solution containing 630 mg of methanesulfonyl chloride was then dropped thereon over a period of 10 minutes, at -15° C. After stirring for 30 minutes at the same temperature, 5 ml of a dichloromethane solution containing 1.14 g of N-formylpiperazine was dropped thereon into the first solution, over a period of 10 minutes, followed by stirring for 1 hour at -5° C. The reaction solution was made alkaline by the addition of saturated sodium bicarbonate solution and then was extracted with dichloromethane (10 ml×3). Next, after washing with saturated brine, the reaction solution was dried with anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain 1.80 g of residue. This was then purified with silica gel column chromatography (elution solvent: ethyl acetate) to obtain 1.68 g of the target compound. Yield: 98%

Workup

  1. additionwas then dropped
  2. customat -15° C
  3. additionwas dropped
  4. waitinto the first solution, over a period of 10 minutes
  5. extractionwas extracted with dichloromethane (10 ml×3)
  6. washNext, after washing with saturated brine
  7. dry with materialthe reaction solution was dried with anhydrous sodium sulfate
  8. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-df88c36f678248039a29430d662a2bfc
Source dataset
uspto-grants-1998_02
Patent number
US05716958

Reaction notes

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