Potassium Carbonate → HCID 15342553, compound

HRID 1720063Notes

Reaction equation

HRID 1720063 reaction equation
NCC[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:11]=2)[NH:6][CH:5]=1.OC1C=C2C(=CC=1)NC=C2.C([O-])([O-])=O.[K+].[K+].BrC(CCC)CC1C=CC=CC=1>CC(=O)CC.C(Cl)Cl>[C:19]1([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:13][C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[NH:6][CH:5]=[CH:4]3)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 160545-HydroxyindoleHCID 15342547HCID 15342547, compoundHCID 22419957HCID 22419957, compound

Product 1

HCID 15342553HCID 15342553, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Synthesis of 3-(2-aminoethyl)-5-(5-phenylpentyloxy)indole was based on the protocols of example 1. A stirred mixture of 5-hydroxyindole (0.5 g, 3.8 mmol), anhydrous K2CO3, (2-bromopentyl)benzene, and a catalytic amount of KI in 2-butanone (40 ml) was heated at reflux overnight under nitrogen. After allowing to cool to room temperature, the reaction mixture was filtered, the flitrate was then concentrated under reduced pressure to give an oil. The oil was taken up in CH2Cl2 (50 ml) and washed successively with 2N-NaOH (1×20 ml) and water (1×20 ml). The organic portion was dried (MgSO4) and the solvent was removed under reduced pressure to give an oil. The oil was purified by column chromatography using a solvent system of CH2Cl2 /Hexane (40:60) to give 5-(5-phenylpentyloxy)indole as an oil.

Workup

  1. temperatureat reflux overnight under nitrogen
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe flitrate was then concentrated under reduced pressure
  4. customto give an oil
  5. washwashed successively with 2N-NaOH (1×20 ml) and water (1×20 ml)
  6. dry with materialThe organic portion was dried (MgSO4)
  7. customthe solvent was removed under reduced pressure
  8. customto give an oil
  9. customThe oil was purified by column chromatography

Sources & evidence

ORD record
ord-f4376d5926e94592a510a1c4af1cea29
Source dataset
uspto-grants-1996_04
Patent number
US05504101

Reaction notes

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