Potassium Carbonate → HCID 22909296, compound

HRID 1379007Notes

Reaction equation

HRID 1379007 reaction equation
ClCC(=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:10]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].[C:29]([C:32]#N)([CH3:31])=[O:30]>>[C:11]1([CH2:10][N:17]2[CH2:22][CH2:21][N:20]([CH:32]([C:29](=[O:30])[CH3:31])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:19][CH2:18]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 694302-OxopropiononitrileHCID 759941-BenzylpiperazineHCID 11469164HCID 11469164, compound

Product 1

HCID 22909296HCID 22909296, compoundYield 89%

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 3-chloro-2-oxopropionate (85.15 g, 0.52 mol), N-benzylpiperazine (6.42 g, 0.49 mol) and K2CO3 (7.1 g, 0.52 mol) in 1L of AcCN was stirred at 50° C. for 24 h. AcCN was removed in vacuo. The residue was partitioned between aqueous Na2CO3 solution (5%, 300 mL) and EtOAC (300 mL×2). The combined EtOAc solution was extracted with 1N aqueous HCl solution. The aqueous solution was separated, neutralized with Na2CO3 to pH 9 and extracted with EtOAc (250 mL×2). The EtOAc layer was separated, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to give 132.60 g (89%) of the desired product as pale yellow liquid. IR(KBr): 3011, 2940, 2810, 1740, 1720, 1650, 1358, 1325, 1250, 1016 cm-1 ; 1H-NMR (80 MHz, CDCl3): δ 1.17-1.24 (t, J=7.1 Hz, 3H, CH3CH2OCO--), 2.05 (s, 3H, CH3CO--), 2.40-2.50 (m, 4H, piperazinyl-H), 2.60-2.70 (m, 4H, piperazinyl-H), 3.45 (s, 2H, --CH2 --Ph), 3.84 (s, 1H, CH3CO--CH--), 4.11-4.18 (q, J=7.1 Hz, 2H, CH3CH2OCO--), 7.10-7.29 (m, 5H, Ph-H) ppm; EI MS m/z (relative-intensity): 304 (M+, 13), 261 (100), 231 (10), 170 (29), 91 (95).

Workup

  1. customAcCN was removed in vacuo
  2. customThe residue was partitioned between aqueous Na2CO3 solution (5%, 300 mL) and EtOAC (300 mL×2)
  3. extractionThe combined EtOAc solution was extracted with 1N aqueous HCl solution
  4. customThe aqueous solution was separated
  5. extractionextracted with EtOAc (250 mL×2)
  6. customThe EtOAc layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2e6334880e414a81b15dd87545cbe56b
Source dataset
uspto-grants-1997_09
Patent number
US05670508

Reaction notes

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