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

HRID 1375950

Reaktionsgleichung

Reaktionsgleichung von HRID 1375950
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

[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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a0db70bc6330407498025c3a96bc8379
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169796B2

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