Diisopropylethylamine → HCID 86688901, compound

HRID 404641Notes

Reaction equation

HRID 404641 reaction equation
CCN(C(C)C)C(C)C.Cl.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][C:13]1=[O:18].Br[CH:20]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(#N)C>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([CH:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:14][C:13]1=[O:18]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 97780Ethyl bromophenylacetateHCID 170607661-Methylpiperazin-2-one--hydrogen chloride (1/1)

Product 1

HCID 86688901HCID 86688901, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

DIPEA (0.52 ml, 2.96 mmol) and 1-methylpiperazin-2-one hydrochloride (0.22 g, 1.48 mmol) were sequentially added to a solution of ethyl 2-bromo-2-phenylacetate (0.22 ml, 1.23 mmol) in acetonitrile (4 ml). The reaction was stirred at room temperature for 1.5 hours. DIPEA (0.13 ml, 0.74 mmol) was added again and the reaction was stirred at room temperature overnight. The solvent was evaporated and the crude was purified by flash chromatography (DCM/Acetone=9/1) to obtain ethyl 2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetate (256 mg, 75% yield) as a yellow oil.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. customThe solvent was evaporated
  3. customthe crude was purified by flash chromatography (DCM/Acetone=9/1)

Sources & evidence

ORD record
ord-f849d05d494e406c90618584cd5db001
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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