Oxalyl chloride → (Rac)-4-cyclopentyl-5,6-dihydro-1-(4-ethylpiperazin-1-ylcarbonyl)-4h-pyrrolo[3,2,1-ij]-quinoline hydrochloride salt

HRID 500455Notes

Reaction equation

HRID 500455 reaction equation
[CH:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8]4=[C:9]([C:16]([C:18](O)=[O:19])=[CH:17][N:7]24)[CH:10]=[CH:11][CH:12]=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:24])=O.[CH2:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH3:28]>ClCCl>[ClH:24].[CH:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8]4=[C:9]([C:16]([C:18]([N:32]5[CH2:33][CH2:34][N:29]([CH2:27][CH3:28])[CH2:30][CH2:31]5)=[O:19])=[CH:17][N:7]24)[CH:10]=[CH:11][CH:12]=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 65578Oxalyl chloride2×HCID 791961-EthylpiperazineHCID 686748084-cyclopentyl-5,6-dihydro4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid

Product 1

HCID 68675643(Rac)-4-cyclopentyl-5,6-dihydro-1-(4-ethylpiperazin-1-ylcarbonyl)-4h-pyrrolo[3,2,1-ij]-quinoline hydrochloride saltYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-cyclopentyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid (342 mg, 1.27 mmol) in dichloromethane (20 ml) was added oxalyl chloride (218 μL, 3.18 mmol) and the reaction mixture stirred for 1 h. A further portion of oxalyl chloride (436 μL, 6.36 mmol) was then added and the reaction stirred overnight. Solvent and excess reagents were then removed in vacuo to leave a green solid. The green solid was dissolved in dichloromethane (20 ml) and N-ethylpiperazine (323 μL, 2.54 mmol) was added dropwise. The resulting reaction mixture was stirred for 1 h and then poured into a separating funnel. The organic layer was washed with saturated potassium bicarbonate solution (20 ml) and brine (20 ml), dried (MgSO4) and the solvent removed in vacuo to leave a brown oil. The oil was purified by flash chromatography eluting with 0-5% (v/v) methanol in dichloromethane to give the title compound (400 mg, 1.09 mmol). 1H NMR (400 MHz, CD3OD) δH 1.31-1.43 (4H, m), 1.45-1.79 (6H, m), 1.87-1.96 (1H, m), 2.05-2.24 (2H, m), 2.30-2.37 (1H, m), 2.90 (1H, dt, J 16.6, 3.9), 3.03-3.20 (3H, m), 3.26 (2H, q, J 7.5), 3.45-3.65 (4H, m), 4.16-4.23 (1H, m), 4.57 (2H, d, J 14.7), 6.99 (1H, d, J 7.1), 7.12 (1H, t, J 8.0), 7.48 (1H, d, J 8.0), 7.76 (1H, s); EsIMS: m/z=366.3 [M+H]+, 252.1.

Workup

  1. stirringthe reaction stirred overnight
  2. customSolvent and excess reagents were then removed in vacuo
  3. customto leave a green solid
  4. customThe resulting reaction mixture
  5. stirringwas stirred for 1 h
  6. additionpoured into a separating funnel
  7. washThe organic layer was washed with saturated potassium bicarbonate solution (20 ml) and brine (20 ml)
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed in vacuo
  10. customto leave a brown oil
  11. customThe oil was purified by flash chromatography
  12. washeluting with 0-5% (v/v) methanol in dichloromethane

Sources & evidence

ORD record
ord-52ef1007b23e49c5802e427821e42402
Source dataset
uspto-grants-2010_08
Patent number
US07772227B2

Reaction notes

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