N-Methylbenzylamine → N-Benzyl-3-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]-N-methylbenzamide

HRID 1836808Notes

Reaction equation

HRID 1836808 reaction equation
[C:1]1([CH:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]([OH:21])=O)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH3:67][NH:68][CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1>ClCCl>[CH2:69]([N:68]([CH3:67])[C:19](=[O:21])[C:18]1[CH:22]=[CH:23][CH:24]=[C:16]([N:13]2[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:11][CH2:12]2)[CH:17]=1)[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1

Participants

6

Reactant 4

HCID 7669N-MethylbenzylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 221804873-[4-(3,3-Diphenyl-1-propyl)piperazin-1-yl]benzoic acid

Product 1

HCID 22180276N-Benzyl-3-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]-N-methylbenzamideYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (0.10 g) prepared in step (c) was dissolved in dichloromethane (2 ml). A BOP reagent (0.10 g) and diisopropylethylamine (0.052 ml) were added to the solution. The mixture was stirred at room temperature for 30 min. N-Methylbenzylamine (0.039 ml) was then added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was extracted with ethyl acetate, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by preparative TLC (hexane:ethyl acetate=1:1) to give 0.072 g (57.3%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washby washing with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was then removed by distillation under the reduced pressure
  6. customThe residue was purified by preparative TLC (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f4b5b500353a41b1bbd0aaebbaf428c5
Source dataset
uspto-grants-2004_08
Patent number
US06777414B1

Reaction notes

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