Diisopropylamine → N-[4-[1-(phenylmethyl)-4-piperidinyl]phenyl]-[1,1'-biphenyl]-2-carboxamide

HRID 852455

Reaction equation

HRID 852455 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7]([OH:9])=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.S(Cl)(Cl)=O.[C:20]1([CH2:26][N:27]2[CH2:32][CH2:31][CH:30]([C:33]3[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=3)[CH2:29][CH2:28]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(NC(C)C)C>C(Cl)Cl.CN(C=O)C>[C:20]1([CH2:26][N:27]2[CH2:28][CH2:29][CH:30]([C:33]3[CH:34]=[CH:35][C:36]([NH:39][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:9])=[CH:37][CH:38]=3)[CH2:31][CH2:32]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 24386Thionyl ChlorideHCID 70357o-Phenylbenzoic acidHCID 224993964-[1-(Phenylmethyl)-4-piperidinyl]-benzenamine

Product 1

HCID 22499413N-[4-[1-(phenylmethyl)-4-piperidinyl]phenyl]-[1,1'-biphenyl]-2-carboxamideYield 112%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

[1,1′-Biphenyl]-2-carboxylic acid (0.25 mol) was dissolved in DCM (500 ml) and DMF (0.5 ml). Thionyl chloride (0.51 mol) was added dropwise. The mixture was stirred and refluxed for 1 hour under nitrogen flow. The solvent was evaporated. DCM (500 ml) was added twice. The solvent was evaporated twice. The residue was dissolved in DCM (200 ml) and then added dropwise at 0° C. to a mixture of 4-[1-(phenylmethyl)-4-piperidinyl]-benzenamine (0.25 mol) and N-(1-methylethyl)-2-propanamine (0.75 mol) in DCM (800 ml). The mixture was brought to room temperature and then stirred at room temperature overnight under nitrogen flow. The mixture was washed three times with water (800 ml). The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 125 g of N-[4-[1-(phenylmethyl)-4-piperidinyl]phenyl]-[1,1′-biphenyl]-2-carboxamide (intermediate 18).

Workup

  1. temperaturerefluxed for 1 hour under nitrogen flow
  2. customThe solvent was evaporated
  3. additionDCM (500 ml) was added twice
  4. customThe solvent was evaporated twice
  5. dissolutionThe residue was dissolved in DCM (200 ml)
  6. customwas brought to room temperature
  7. stirringstirred at room temperature overnight under nitrogen flow
  8. washThe mixture was washed three times with water (800 ml)
  9. customThe organic layer was separated
  10. customdried
  11. filtrationfiltered
  12. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3c5b4a952a3e4e38be826265506ff424
Source dataset
uspto-grants-2007_08
Patent number
US07253157B2

Linked notes

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