Potassium Carbonate → HCID 18782752, compound

HRID 1420711Notes

Reaction equation

HRID 1420711 reaction equation
[C:1]1([C:7]2([OH:13])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[Cl:20][CH2:21][CH:22]([OH:37])[CH2:23][N:24]1[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2>CC(C)CC(=O)C>[ClH:20].[CH:26]1[C:25]2[N:24]([CH2:23][CH:22]([OH:37])[CH2:21][N:10]3[CH2:11][CH2:12][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([OH:13])[CH2:8][CH2:9]3)[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]=2[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 963874-Phenylpiperidin-4-olHCID 2775474HCID 2775474, compound

Product 1

HCID 18782752HCID 18782752, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

4-Phenylpiperidin-4-ol (0.77 g, 0.0043 mol) was dissolved in 4-methyl-pentan-2-one (40 mL), K2CO3 (1.59 g, 0.0116 mol) and 9-(3-chloro-2-hydroxy-1-propyl)carbazole (0.75 g, 0.0029 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)), and further purified on a silica gel column (Eluent: Gradient 1) ethyl acetate/methanol (20:1); 2) ethyl acetate/methanol (3:1); 3) CH2Cl2 /methanol (9:1)). The product was acidified with 2M HCl(g) in diethyl ether, to give the title compound 0.77 g (61%). M.p. decomposes at 193-224° 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))
  5. customfurther purified on a silica gel column (Eluent: Gradient 1) ethyl acetate/methanol (20:1)

Sources & evidence

ORD record
ord-5d4a9d9c0c0843e2bdc281c6299f208d
Source dataset
uspto-grants-2000_06
Patent number
US06071932

Reaction notes

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