Potassium Carbonate → HCID 18001243, compound

HRID 478202Notes

Reaction equation

HRID 478202 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][CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:17].[C:27]1([CH:24]2[CH2:23][CH2:22][N:21]([CH2:20][CH2:19][CH2:18][N:13]3[CH2:14][CH2:15][CH:10]([C:3]4[C:4]5[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=5)[NH:1][CH:2]=4)[CH2:11][CH2:12]3)[CH2:26][CH2:25]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 203688Piperidine, 1-(3-chloropropyl)-4-phenyl-, hydrochlorideHCID 7022353-(4-Piperidinyl)-1H-indole

Product 1

HCID 18001243HCID 18001243, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspended solution of 4-(3-indolyl)piperidine (2.0 g, 10 mmol) and 1-(3-chloropropyl)-4-phenylpiperidine hydrochloride (3.1 g, 11.2 mmol) in DMF (60 mL) was added potassium carbonate (5.5 g, 40 mmol), and the mixture was stirred at 100° C. for 4 hours. After the precipitated salt was filtered off, the filtrate was concentrated, water (50 mL) was added to the filtrate, and the mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the chloroform layer was concentrated to afford a crude product. The crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; chloroform) and was then recrystallized from ethyl acetate to afford a free form (1.6 g, yield: 40%) of the title compound as white crystals. After adding hydrochloric acid/methanol to a solution of the free form (1.6 g) in methanol, the mixture was concentrated and was then recrystallized from methanol/ether to afford the title compound (1.8 g) as white crystals.

Workup

  1. filtrationAfter the precipitated salt was filtered off
  2. concentrationthe filtrate was concentrated
  3. additionwater (50 mL) was added to the filtrate
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. concentrationthe chloroform layer was concentrated
  7. customto afford a crude product
  8. customThe crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; chloroform)
  9. customwas then recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0a2cf5f9c1ef416083e1abf734d75bb4
Source dataset
uspto-grants-2003_11
Patent number
US06642228B1

Reaction notes

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