Ethyl Acetate → HCID 58786549, compound

HRID 1376033Notes

Reaction equation

HRID 1376033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:9]([NH2:11])=[O:10].[CH2:18]1[CH2:22]OC[CH2:19]1.O.[C:24]([O-:27])([O-])=[O:25].[K+].[K+].[CH3:30]COC(C)=O>>[C:18]([O:27][C:24]([N:15]1[CH2:16][CH2:17][N:12]([CH:8]([C:9](=[O:10])[NH2:11])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:13][CH2:14]1)=[O:25])([CH3:19])([CH3:22])[CH3:30]

Participants

5

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 21881883Oxolane--water (1/1)HCID 58786666HCID 58786666, compound

Product 1

HCID 58786549HCID 58786549, compoundYield 56%

Procedure

To 2-(2-Chloro-phenyl)-2-piperazin-1-yl-acetamide (461) (0.64 g, 2.52 mmol) in a 1:1 mixture of THF/H2O (5.0 mL) was added K2CO3 (0.77 g, 5.55 mmol). The mixture was allowed stir for 15 min at room temperature. Boc-anhydride (0.60 g, 2.72 mmol) was then added and the reaction was allowed to stir at room temperature for 18 h. The reaction mixture was then diluted with EtOAc (50 mL) and washed with sat. NaHCO3 (50 mL) and brine (50 mL). The crude material was purified by chromatography (silica gel 60 mesh, eluting with 5% MeOH in CHCl3) yielding 0.50 g (56%) pure product.

Workup

  1. stirringto stir at room temperature for 18 h
  2. washwashed with sat. NaHCO3 (50 mL) and brine (50 mL)
  3. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-76c538855acf43289887b8d0534eb597
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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