Triethylamine → HCID 17376141, compound

HRID 1597429Notes

Reaction equation

HRID 1597429 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:5])[CH3:2].[S:13](Cl)([CH3:16])(=[O:15])=[O:14].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][S:13]([N:10]1[CH2:9][CH2:8][N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:12][CH2:11]1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 207112Ethyl piperazine-1-acetate

Product 1

HCID 17376141HCID 17376141, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice cold solution of 1-ethoxycarbonylmethylpiperazine (5 g, 29 mmol), mesyl chloride (3.37 mL, 43.5 mmol) and triethyl amine (6.05 mL, 43.5 mmol) in CH2Cl2 (150 mL) was stirred at 0° C. for 5 min then at rt for 30 min, then partitioned between CH2Cl2 and aq. sat. NH4Cl. The organics were washed with aq. NaHCO3, brine, dried (Na2SO4), filtered and concentrated to give 6.88 g of the title compound. MS (APCI) m/z 251 (M+H)+.

Workup

  1. custompartitioned between CH2Cl2 and aq. sat. NH4Cl
  2. washThe organics were washed with aq. NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7afe843a3ad3443fa836767e01fd92fa
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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