Potassium Carbonate → HCID 18782775, compound

HRID 1420710Notes

Reaction equation

HRID 1420710 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:15])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[Cl:22][CH2:23][CH:24]([OH:39])[CH2:25][N:26]1[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2>CC(C)CC(=O)C>[ClH:22].[CH:28]1[C:27]2[N:26]([CH2:25][CH:24]([OH:39])[CH2:23][N:12]3[CH2:11][CH2:10][C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)([OH:15])[CH2:14][CH2:13]3)[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2775474HCID 2775474, compoundHCID 132505484-(4-Methoxyphenyl)piperidin-4-ol

Product 1

HCID 18782775HCID 18782775, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

4-(4-Methoxyphenyl)piperidin-4-ol (0.50 g, 0.0024 mol) was dissolved in 4-methyl-pentan-2-one (35 mL), K2CO3 (1.33 g, 0.0096 mol) and 9-(3-chloro-2-hydroxy-1-propyl)carbazole (0.42 g, 0.0016 mol) were added, and the resulting mixture was stirred at reflux temperature overnight. The reaction mixture was filtered and the solvent was removed in vacuo. The residual oil was purified on a silica gel column (Eluent: CH2Cl2 /ethanol/25% NH4OH (aq) (92.75:7:0.25)). The product was acidified with 2M HCl(g) in diethyl ether, to give the title compound 0.39 g (51%). M.p. decomposes at 125° C.

Workup

  1. temperatureat reflux temperature overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed in vacuo
  4. customThe residual oil was purified on a silica gel column (Eluent: CH2Cl2 /ethanol/25% NH4OH (aq) (92.75:7:0.25))

Sources & evidence

ORD record
ord-995b3d71656e40918ebddc63628fc5c1
Source dataset
uspto-grants-2000_06
Patent number
US06071932

Reaction notes

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