Potassium Carbonate → HCID 12790165, compound

HRID 2198527Notes

Reaction equation

HRID 2198527 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.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([OH:26])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][N:23]2[CH2:22][CH2:21][C:20]([C:17]3[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=3)([OH:26])[CH2:25][CH2:24]2)=[CH:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 769243-(2-Bromoethyl)indole

Product 1

HCID 12790165HCID 12790165, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2-bromoethyl)indole (1.06 g; 4.73 mM), 4-(p-chlorophenyl)piperidin-4-ol (1.0 g; 4.72 mM), potassium carbonate (0.75 g; 5.42 mM) and dimethylformamide (12 ml) was stirred in an oil-bath maintained at 75° for 19.5 hours under a nitrogen blanket. The mixture was poured onto water (50 ml) and cooled in ice. The sticky, yellow solid which formed was filtered off and washed well with water. It was then promptly transferred to a new flask (the solid tended to gum) and dissolved in ethanol, acidified with ethanolic HCl and the solvents evaporated. The residue was crystallised from iso-propanol/ethyl acetate, then twice triturated well with ethanol/ethyl acetate. Filtration gave the title compound as the hydrochloride (0.99 g; 53.5%) as very pale pink plates, m.p. 248°-252° (dec; decomposition occurred above 235°).

Workup

  1. temperaturemaintained at 75° for 19.5 hours under a nitrogen blanket
  2. additionThe mixture was poured onto water (50 ml)
  3. temperaturecooled in ice
  4. customThe sticky, yellow solid which formed
  5. filtrationwas filtered off
  6. washwashed well with water
  7. customIt was then promptly transferred to a new flask
  8. dissolutiondissolved in ethanol
  9. customthe solvents evaporated
  10. customThe residue was crystallised from iso-propanol/ethyl acetate
  11. customtwice triturated well with ethanol/ethyl acetate
  12. filtrationFiltration

Sources & evidence

ORD record
ord-58915e9d97c64c50bb86884518d00d5e
Source dataset
uspto-grants-1982_11
Patent number
US04358456

Reaction notes

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