Sodium Hydroxide → 4-[(Methyl)(methylsulfonyl)amino]-N-[[4-phenyl-1-(phenylmethyl)piperazin-2-yl]methyl]benzamide

HRID 728937Notes

Reaction equation

HRID 728937 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]([CH2:20][NH2:21])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Al](C)C.C[O:27][C:28](=O)[C:29]1[CH:34]=[CH:33][C:32]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[CH:31][CH:30]=1.[OH-].[Na+]>>[CH3:40][N:35]([S:36]([CH3:39])(=[O:38])=[O:37])[C:32]1[CH:31]=[CH:30][C:29]([C:28]([NH:21][CH2:20][CH:9]2[CH2:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11][N:10]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:27])=[CH:34][CH:33]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 11044210C-(1-Benzyl-4-phenyl-piperazin-2-yl)-methylamineHCID 149988164-[(Methyl)(methylsulfonyl)amino]benzoic acid methyl esterHCID 16682925Trimethylaluminum

Product 1

HCID 149988174-[(Methyl)(methylsulfonyl)amino]-N-[[4-phenyl-1-(phenylmethyl)piperazin-2-yl]methyl]benzamide

Procedure

To 4-phenyl-1-(phenylmethyl)-2-piperazinemethanamine (6.95 g, 24.7 mmol) intoluene (130 mL) at 0° C. add trimethylaluminum (2.0M in toluene, 16.2 mL, 32.4 mmol). Allow the reaction to warm to room temperature and add 4-[(methyl)(methylsulfonyl)amino]benzoic acid methyl ester (6.91 g, 28.4 mmol). Heat the reaction and monitor the progress by thin-layer chromatography. Upon completion make the solution basic with aqueous NaOH and extract with EtOAc. Remove the solvent in vacuo. Flash chromatograph the residue on silica gel with EtOAc/hexane (2/1) to obtain the title compound.

Workup

  1. customthe reaction
  2. temperatureHeat
  3. customthe reaction
  4. extractionextract with EtOAc
  5. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-02d28f9ba84f459fb47b534349d6d816
Source dataset
uspto-grants-1991_09
Patent number
US05051422

Reaction notes

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