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

HRID 1375945Notes

Reaction equation

HRID 1375945 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. washwashed
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was triturated in DIPE
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-805bb22685e4417e9bbd3fdfa00dbf00
Source dataset
uspto-grants-2007_01
Patent number
US07169796B2

Reaction notes

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