Sodium Bicarbonate → 1-Piperazin-1-yl-1,9a-dihydro-quinolizin-4-one

HRID 1192389Notes

Reaction equation

HRID 1192389 reaction equation
C(OC([C:6]1[C:15](=[O:16])[N:14]2[CH:9]([CH:10]=[CH:11][CH:12]=[CH:13]2)[CH:8]([N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)[CH:7]=1)=O)C.C([O-])(O)=O.[Na+]>Cl>[N:17]1([CH:8]2[CH:9]3[N:14]([CH:13]=[CH:12][CH:11]=[CH:10]3)[C:15](=[O:16])[CH:6]=[CH:7]2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 675389481-(4-tert-Butoxycarbonyl-piperazin-1-yl)-4-oxo-1,9a-dihydro-4H-quinolizine-3-carboxylic acid ethyl ester

Product 1

HCID 675397771-Piperazin-1-yl-1,9a-dihydro-quinolizin-4-oneYield 41%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1-(4-tert-Butoxycarbonyl-piperazin-1-yl)-4-oxo-1,9a-dihydro-4H-quinolizine-3-carboxylic acid ethyl ester (0.320 g, 0.797 mmol) in concentrated HCl (5 mL) was refluxed for 30 minutes. After cooling, the reaction was basified with aqueous NaHCO3 solution and thoroughly extracted with DCM. The combined organic layers were washed with brine, dried and concentrated to give 1-Piperazin-1-yl-1,9a-dihydro-quinolizin-4-one (0.075 g, 41%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 9.16 (d, J=7.2 Hz, 1H), 8.20 (d, J=9.2 Hz, 1H), 7.71 (d, J=9.6 Hz, 1H), 7.37 (t, J=7.2 Hz, 1H), 7.03 (t, J=6.4 Hz, 1H), 6.61 (d, J=9.2 Hz, 1H), 3.07 (m, 4H), 2.87 (m, 4H). LCMS (APCI+) m/z 230 [M+H]+; Rt=0.29 min.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperatureAfter cooling
  3. extractionthoroughly extracted with DCM
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d33d4cfce72949a6b897b332b0a2da64
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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