[1,1'-Biphenyl]-2-carbonyl chloride → N-[4-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]phenyl]-[1,1'-biphenyl]-2-carboxamide

HRID 852450Notes

Reaction equation

HRID 852450 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7](Cl)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:16]1([CH2:22][N:23]2[CH2:28][CH:27]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.C(N(CC)CC)C>[C:16]1([CH2:22][N:23]2[CH2:24][CH:25]=[C:26]([C:29]3[CH:30]=[CH:31][C:32]([NH:35][C:7]([C:2]4[C:1]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=5)=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:8])=[CH:33][CH:34]=3)[CH2:27][CH2:28]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 12563768[1,1'-Biphenyl]-2-carbonyl chlorideHCID 224994164-[1,2,3,6-Tetrahydro-1-(phenylmethyl)-4-pyridinyl]benzenamine

Product 1

HCID 22499381N-[4-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]phenyl]-[1,1'-biphenyl]-2-carboxamideYield 92.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

[1,1′-Biphenyl]-2-carbonyl chloride (0.05 mole) was added dropwise to a stirring mixture of 4-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]benzenamine (0.045 mole) in THF (300 ml) and triethylamine (25 ml). 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. The precipitate was filtered off and dried, yielding 18.5 g of N-[4-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]phenyl]-[1,1′-biphenyl]-2-carboxamide (intermediate 11, melting point 142° C.).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in DCM
  3. customThe organic layer was separated
  4. washwashed
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was triturated in DIPE
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-5bf5af35004d41899d8c212f082389a7
Source dataset
uspto-grants-2007_08
Patent number
US07253157B2

Reaction notes

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