HCID 19755014, compound → HCID 19755017, compound

HRID 728978Notes

Reaction equation

HRID 728978 reaction equation
[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:35]=[CH:34][C:10]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][N:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:18][CH2:17][N:16]2CC2C=CC=CC=2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4]>[OH-].[OH-].[Pd+2].CO>[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][N:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:18][CH2:17][NH:16]2)=[O:12])=[CH:34][CH:35]=1)(=[O:4])=[O:5]

Participants

4

Reactant 1

HCID 19755014HCID 19755014, compound

Product 1

HCID 19755017HCID 19755017, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To methanol (400 mL) add 4-[(methylsulfonyl)amino]-N-[[4-phenyl-1-(phenylmethyl)piperazin-2-yl]methyl]benzamide hydrochloride (40 g, 77 mmol) and Pd(OH)2 (2.0 g). When the addition is complete, place the reaction mixture on a Parr hydrogenator at 50 p.s.i. of H2 and shake. Monitor the progress of the reaction by thin-layer chromatography. Upon completion of the reaction, remove the catalyst by suction filtration through celite. Wash the pad with methanol. Remove the solvent in vacuo to obtain a residue. Recrystallize from methanol to provide the title compound.

Workup

  1. additionWhen the addition
  2. customMonitor the progress of the reaction by thin-layer chromatography
  3. customUpon completion of the reaction
  4. customremove the catalyst
  5. filtrationby suction filtration through celite
  6. washWash the pad with methanol
  7. customRemove the solvent in vacuo
  8. customto obtain a residue
  9. customRecrystallize from methanol

Sources & evidence

ORD record
ord-5025e089404f455eb31c2949aed7e032
Source dataset
uspto-grants-1991_09
Patent number
US05051422

Reaction notes

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