Potassium Carbonate → 1-(1-(3-(4-Indol-3-ylpiperidyl)propyl)-3-piperidyl)-4-methoxybenzene Hydrochloride

HRID 478203Notes

Reaction equation

HRID 478203 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:2]1.Cl.[Cl:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[ClH:17].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27]4[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=4)[CH2:22]3)[CH2:12][CH2:11]2)=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 180012091-(3-Chloropropyl)-3-(4-methoxyphenyl)piperidine hydrochloride

Product 1

HCID 180012601-(1-(3-(4-Indol-3-ylpiperidyl)propyl)-3-piperidyl)-4-methoxybenzene HydrochlorideYield 98.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspended solution of 4-(3-indolyl)piperidine (48 mg, 0.24 mmol) and 1-(3-chloropropyl)-3-(4-methoxyphenyl)piperidine hydrochloride (61 mg, 0.2 mmol) in acetonitrile (13 mL) was added potassium carbonate (111 mg, 0.8 mmol), and the resulting mixture was refluxed for 12 hours. After the precipitated salt was filtered off, the filtrate was concentrated, and the resulting crude product was purified by column chromatography on a silica gel (eluent; chloroform:ammonia-saturated chloroform=10:1→3:1→1:2) to afford a free form (92 mg) of the title compound as a colorless viscous oil. After adding hydrochloric acid/methanol to a solution of the free form in methanol, the mixture was concentrated and was then freeze-dried to afford the title compound (81 mg, yield: 80%) as a white amorphous solid.

Workup

  1. temperaturethe resulting mixture was refluxed for 12 hours
  2. filtrationAfter the precipitated salt was filtered off
  3. concentrationthe filtrate was concentrated
  4. customthe resulting crude product was purified by column chromatography on a silica gel (eluent; chloroform:ammonia-saturated chloroform=10:1→3:1→1:2)

Sources & evidence

ORD record
ord-48c1da86bfff4693b205fa9e7154138b
Source dataset
uspto-grants-2003_11
Patent number
US06642228B1

Reaction notes

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