Potassium Carbonate → HCID 18706979, compound

HRID 1422101Notes

Reaction equation

HRID 1422101 reaction equation
[CH2:1]([C:3]1[C:11]2[N:6]3[C:7](=[C:12]([C:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=4)[CH:13]=[C:5]3[C:4]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[CH:8]=[CH:9][CH:10]=2)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>CC(C)=O.[I-].[Na+]>[CH2:1]([C:3]1[C:11]2[N:6]3[C:7](=[C:12]([C:14]4[CH:15]=[CH:16][C:17]([O:20][CH2:37][CH2:38][N:39]5[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]5)=[CH:18][CH:19]=4)[CH:13]=[C:5]3[C:4]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[CH:8]=[CH:9][CH:10]=2)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 18706985HCID 18706985, compound

Product 1

HCID 18706979HCID 18706979, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 180AcetoneSolvent

Procedure

1-Ethyl-4-(4-hydroxyphenyl)-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine (0.368 g, 1.0 mmol), potassium carbonate (2.07 g, 15.9 mmol), sodium iodide (8 mg, 0.05 mmol) and 1-(2-chloroethyl)piperidine hydrochloride was suspended in 70 ml of dry acetone. The mixture was refluxed for 6 hours, and stirred at room temperature for 16 hours. Remaining salts were filtered off, and the solvent was evaporated. The crude product was purified by column chromatography over silica gel 60, using 15% of methanol in dichloromethane as the eluent. Fractions containing the product were combined and the solvent was evaporated. The crude product was crystallised from diethyl ether and petroleum ether to afford 0.326 g (68%) of the title compound. 1H--NMR (CDCl3, 200 MHz) δ: 1.40-1.70 (m,9 H); 2.50-2.60 (m, 4 H); 2.82 (t, 2 H); 3.26 (q, 2 H); 3.91 (s, 3 H); 4.19 (t, 2 H); 7.01-7.13 (m, 4 H); 7.62-7.83 (m, 6 H); 7.92 (d, 1 H); 8.14 (d, 1 H).

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. filtrationRemaining salts were filtered off
  3. customthe solvent was evaporated
  4. customThe crude product was purified by column chromatography over silica gel 60
  5. additionFractions containing the product
  6. customthe solvent was evaporated
  7. customThe crude product was crystallised from diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-72d8a0c728034c1d83706db9056c22ae
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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