Potassium Carbonate → HCID 9819146, compound

HRID 1031492Notes

Reaction equation

HRID 1031492 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:13][O:14][C:15]1[C:16]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[N:17][CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][N:24]2[CH2:25][CH2:26][N:21]([C:16]3[C:15]([O:14][CH3:13])=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:22][CH2:23]2)=[CH:5]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 769243-(2-Bromoethyl)indoleHCID 127904951-(3-Methoxypyridin-2-yl)piperazine

Product 1

HCID 9819146HCID 9819146, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(2-bromoethyl)indole (2.00 g), 1-(3-methoxy-2-pyridinyl)piperazine (1.72 g), micropulverized K2CO3 (2.46 g) and tetrabutylammonium hydrogen sulfate (0.15 g), in acetonitrile (50 mL) was heated at reflux under N2 atmosphere for 5 h. The excess acetonitrile was removed under reduced pressure and water (10 mL) was added to the concentrate. The aqueous phase was extracted with CH2Cl2 (3×50 mL). The combined CH2Cl2 extracts were washed with sat. NaCl solution, dried with anhydrous K2CO3, and concentrated under reduced pressure. Silica gel chromatography (CH2Cl2 /MeOH; 96.4) of the residue yielded the free base of the desired Ia product (1.32 g; 44%).

Workup

  1. temperatureat reflux under N2 atmosphere for 5 h
  2. customThe excess acetonitrile was removed under reduced pressure and water (10 mL)
  3. additionwas added to the concentrate
  4. extractionThe aqueous phase was extracted with CH2Cl2 (3×50 mL)
  5. washThe combined CH2Cl2 extracts were washed with sat. NaCl solution
  6. dry with materialdried with anhydrous K2CO3
  7. concentrationconcentrated under reduced pressure
  8. customSilica gel chromatography (CH2Cl2 /MeOH; 96.4) of the residue yielded the free base of the desired Ia product (1.32 g; 44%)

Sources & evidence

ORD record
ord-47d2688a599146409f1ec0b4d76a2a46
Source dataset
uspto-grants-1990_09
Patent number
US04954502

Reaction notes

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