Triethylamine → HCID 58561856, compound

HRID 390988Notes

Reaction equation

HRID 390988 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:21][N:22]1[CH:26]=[C:25]([S:27](Cl)(=[O:29])=[O:28])[N:24]=[CH:23]1>C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([S:27]([C:25]2[N:24]=[CH:23][N:22]([CH3:21])[CH:26]=2)(=[O:29])=[O:28])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27368871-methyl-1H-imidazole-4-sulfonyl chloride

Product 1

HCID 58561856HCID 58561856, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N-Boc-piperazine (500 mg) in DCM (10 ml) was added triethylamine (450 μl) and 1-methylimidazole-4-sulfonyl chloride (524 mg). The reaction mixture was stirred at room temperature overnight, then partitioned between dichloromethane and water, washed with brine, organics were dried over MgSO4, filtered and volatiles removed in vacuo to give 4-(1-methylimidazole-4-sulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (730 mg).

Workup

  1. custompartitioned between dichloromethane and water
  2. washwashed with brine
  3. dry with materialorganics were dried over MgSO4
  4. filtrationfiltered
  5. customvolatiles removed in vacuo

Sources & evidence

ORD record
ord-05e9832ce1d4489cab19964d52ac7100
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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