Triethylamine → HCID 59712100, compound

HRID 2222220Notes

Reaction equation

HRID 2222220 reaction equation
O[CH2:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][CH:6]1[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]([CH3:14])[C:7]1=[O:15].CCN(CC)CC.S([Cl:31])(C)(=O)=O.[Li+].[Cl-]>CN(C=O)C>[CH3:12][N:11]1[C:10](=[O:13])[CH2:9][N:8]([CH3:14])[C:7](=[O:15])[CH:6]1[CH2:5][C:4]1[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=1[CH2:2][Cl:31]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 433294Lithium ChlorideHCID 59712097HCID 59712097, compound

Product 1

HCID 59712100HCID 59712100, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[2-(hydroxymethyl)benzyl]-1,4-dimethylpiperazine-2,5-dione (1.48 g, 5.64 mmol) and Et3N (1.57 ml, 11.28 mmol) in DMF was cooled to 0° C. Mesyl chloride was added via syringe at 0° C. and the stirring reaction allowed to warm to ambient temperature via bath melting overnight. More Et3N (2 equivalents) and mesyl chloride (1.1 equivalents) was added at 0° C. and the stirring reaction allowed to warm to ambient temperature via bath melting for 6 hours. LiCl (478 mg, 11.28 mmol) was added and the reaction stirred at ambient temperature for 1.5 hours. The mixture was partitioned between NH4Cl and EtOAc and extracted with EtOAc (3×). The combined organic solutions were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by normal phase chromatography (0-3% MeOH(NH3)/CH2Cl2) to give a yellow oil (1.47 g).

Workup

  1. customthe stirring reaction
  2. customthe stirring reaction
  3. temperatureto warm to ambient temperature via bath
  4. waitmelting for 6 hours
  5. customThe mixture was partitioned between NH4Cl and EtOAc
  6. extractionextracted with EtOAc (3×)
  7. washThe combined organic solutions were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe crude product was purified by normal phase chromatography (0-3% MeOH(NH3)/CH2Cl2)

Sources & evidence

ORD record
ord-0d4cc3675a5f4b04a5f950352a0f1963
Source dataset
uspto-grants-2008_05
Patent number
US07371754B2

Reaction notes

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