Diisopropylethylamine → HCID 23447416, compound

HRID 1840578Notes

Reaction equation

HRID 1840578 reaction equation
[N:1]1([C:6]2[CH:19]=[CH:18][C:9]([CH2:10][N:11]3[CH2:16][CH2:15][NH:14][CH2:13][C:12]3=[O:17])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.Cl[S:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])(=[O:32])=[O:31]>ClCCl>[N:1]1([C:6]2[CH:19]=[CH:18][C:9]([CH2:10][N:11]3[CH2:16][CH2:15][N:14]([S:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])(=[O:32])=[O:31])[CH2:13][C:12]3=[O:17])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11435213Methyl (chlorosulfonyl)acetateHCID 23447329HCID 23447329, compound

Product 1

HCID 23447416HCID 23447416, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[4-(1-imidazolyl)benzyl]piperazin-2-one (586 mg) and diisopropylethylamine (388 mg) in dichloromethane (10 ml) was added dropwise, under ice-cooling, a solution of methyl chlorosulfonylacetate (380 mg) in dichloromethane (10 ml), and the mixture was stirred at room temperature overnight. The reaction solution was washed with 0.5N hydrochloric acid and saturated brine, dried and concentrated, and the residue was purified with silica gel column chromatography (eluent: methanol/dichloromethane=1/10) to give colorless oil of 1-[4-(1-imidazolyl)benzyl]-4-methoxycarbonylmethylsulfonyl-2-oxopiperazine (0.170 g).

Workup

  1. temperaturecooling
  2. washThe reaction solution was washed with 0.5N hydrochloric acid and saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customthe residue was purified with silica gel column chromatography (eluent: methanol/dichloromethane=1/10)

Sources & evidence

ORD record
ord-a37c5723a1f4472daba3b9be59edcf98
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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