4-(4-Benzylpiperazin-1-yl)aniline → N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-[1,1'-biphenyl]-2-carboxamide

HRID 1804428Notes

Reaction equation

HRID 1804428 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:22]([C:27](Cl)=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=1>C1COCC1.C(N(CC)CC)C>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:27]([C:22]4[C:21]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:28])=[CH:18][CH:19]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 7372594-(4-Benzylpiperazin-1-yl)anilineHCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Product 1

HCID 22499373N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-[1,1'-biphenyl]-2-carboxamideYield 1.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-[4-(phenylmethyl)-1-piperazinyl]-benzenamine (0.12 mole) in THF (300 ml) and triethylamine (50 ml) was stirred. [1,1′-Biphenyl]-2-carbonyl chloride (0.12 mole) was added dropwise. The mixture was stirred overnight. The solvent was evaporated. The residue was dissolved in DCM. The organic layer was separated, washed, dried, filtered and the solvent was evaporated. The residue was triturated in DIPE/2-propanol. The precipitate was filtered off and dried. A part (1 g) of this fraction was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1). The pure fractions were collected and the solvent was evaporated. The residue was triturated in DIPE. The precipitate was filtered off and dried, yielding 0.84 g of N-[4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-[1,1′-biphenyl]-2-carboxamide (intermediate 9, melting point 162° C.).

Workup

  1. stirringThe mixture was stirred overnight
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. customThe organic layer was separated
  5. washwashed
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was triturated in DIPE/2-propanol
  10. filtrationThe precipitate was filtered off
  11. customdried
  12. customA part (1 g) of this fraction was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1)
  13. customThe pure fractions were collected
  14. customthe solvent was evaporated
  15. customThe residue was triturated in DIPE
  16. filtrationThe precipitate was filtered off
  17. customdried

Sources & evidence

ORD record
ord-0b9c49bc680d4d77af990c173d20a257
Source dataset
uspto-grants-2013_01
Patent number
US08354402B2

Reaction notes

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