Potassium Carbonate → 1-[3-(9H-Carbazol-9-yl)propyl]-4-(2-methoxyphenyl)piperidin-4-ol--hydrogen chloride (1/1)

HRID 1420700Notes

Reaction equation

HRID 1420700 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.BrCCCN1C2C=CC=CC=2C2C1=CC=CC=2.[CH3:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]1([OH:49])[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1.C([O-])([O-])=O.[K+].[K+]>CC(CC(C)C)=O>[ClH:1].[CH:16]1[C:17]2[N:5]([CH2:4][CH2:3][CH2:2][N:46]3[CH2:45][CH2:44][C:43]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[O:36][CH3:35])([OH:49])[CH2:48][CH2:47]3)[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 106321344-(2-methoxyphenyl)piperidin-4-olHCID 86755445HCID 86755445, compound

Product 1

HCID 187827601-[3-(9H-Carbazol-9-yl)propyl]-4-(2-methoxyphenyl)piperidin-4-ol--hydrogen chloride (1/1)Yield 68%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

Compound 1 (0.879 g, 0.0036 mol ) was dissolved in methylisobutylketone (MIBK) (80 mL). 4-(2-Methoxyphenyl)piperidin-4-ol (1.123 g, 0.0054 mol) and K2CO3 (1.99 g, 0.0145 mol) were added. The resulting mixture was stirred at reflux temperature for 12 h. The reaction mixture was filtered and the solvent evaporated 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 diethylether, to give the title compound 1.1 g (68%). M.p. decomposes at 228° C.

Workup

  1. temperatureat reflux temperature for 12 h
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent evaporated 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-286145297339474b930b40a92e0eeb8d
Source dataset
uspto-grants-2000_06
Patent number
US06071932

Reaction notes

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