Hydrochloric Acid → HCID 131720264, compound

HRID 1490332Notes

Reaction equation

HRID 1490332 reaction equation
[O:1]1CCCC1.[CH3:6][O:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH2:16][CH2:17][C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])[CH2:22][CH2:21]2)=O)=[C:10]([N:34]2[CH:38]=[CH:37][CH:36]=[CH:35]2)[CH:9]=1.O.[ClH:40]>C(O)C>[OH2:1].[ClH:40].[ClH:40].[CH3:6][O:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH2:16][CH2:17][CH2:18][N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])[CH2:22][CH2:21]2)=[C:10]([N:34]2[CH:38]=[CH:37][CH:36]=[CH:35]2)[CH:9]=1.[CH3:6][O:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH2:16][CH2:17][CH2:18][N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])[CH2:22][CH2:21]2)=[C:10]([N:34]2[CH:38]=[CH:37][CH:36]=[CH:35]2)[CH:9]=1.[ClH:40].[ClH:40]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 21481012HCID 21481012, compound

Product 1

HCID 131720264HCID 131720264, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 100 ml of tetrahydrofuran were added 18 ml of 1.0M borane-tetrahydrofuran complex and 1.14 g of 1-(3-(4,5-dimethoxy-2-(1-pyrrolyl)phenyl)-1-oxopropyl)-4-(2-methoxyphenyl)piperazine at room temperature, and the mixture was heated under reflux for 27 hours. Since it was found that the reaction had not completed, 10 ml of the borane-tetrahydrofuran complex was further added, and the refluxing was continued for additional 9 hours. After cooling to room temperature, 10 ml of water was added to the reaction mixture, and the solvent was removed under reduced pressure. To the residue was added 35 ml of 5% hydrochloric acid, followed by heating at 50° to 60° C. for 2 hours. The reaction mixture was dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform) to yield 780 mg of a pale yellow oily substance, which was dissolved in 15 ml of ethanol, 1.0 ml of concentrated hydrochloric acid was added thereto, and the solvent was removed under reduced pressure. Recrystallization of the residue from ethanol-ethyl ether yielded 500 mg of the title compound as a colorless prism crystal.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 27 hours
  3. addition10 ml of the borane-tetrahydrofuran complex was further added
  4. customthe solvent was removed under reduced pressure
  5. additionTo the residue was added 35 ml of 5% hydrochloric acid
  6. temperatureby heating at 50° to 60° C. for 2 hours
  7. dry with materialThe reaction mixture was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography (chloroform)
  10. customto yield 780 mg of a pale yellow oily substance, which
  11. customthe solvent was removed under reduced pressure
  12. customRecrystallization of the residue from ethanol-ethyl ether

Sources & evidence

ORD record
ord-a0840ccd29164afab10d4993e0a7985c
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

Loading…