Dimethylformamide → N,N-dimethyl-4-phenylpiperidine-4-carboxamide

HRID 1739110

Reaktionsgleichung

Reaktionsgleichung von HRID 1739110
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.Cl.[CH3:9]NC.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2N=N1.[CH3:39][N:40]([CH:42]=[O:43])[CH3:41]>C(Cl)Cl>[CH3:39][N:40]([CH3:41])[C:42]([C:9]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:5][CH2:4][NH:3][CH2:6][CH2:7]1)=[O:43]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Produkt 1

HCID 417393N,N-dimethyl-4-phenylpiperidine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

8.1 g of triethylamine and then 4.9 g of dimethylamine hydrochloride are added to a solution of 6.11 g of the compound obtained in step A of PREPARATION 1.21 in 20 ml of DCM and 20 ml of DMF. The mixture is cooled in an ice bath, 9.73 g of BOP are added and the mixture is left stirring for 3 hours while allowing the temperature to rise to RT. The mixture is concentrated under vacuum, the residue is extracted with ether, the organic phase is washed with water, with a pH 2 buffer solution, with 10% NaOH solution, with water and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. 6.45 g of the expected product are obtained.

Aufarbeitung

  1. temperatureThe mixture is cooled in an ice bath
  2. waitthe mixture is left
  3. customto rise to RT
  4. concentrationThe mixture is concentrated under vacuum
  5. extractionthe residue is extracted with ether
  6. washthe organic phase is washed with water, with a pH 2 buffer solution, with 10% NaOH solution, with water and with saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. customthe solvent is evaporated off under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-66f1efa0e0d8446c8561ed97495564ec
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965580

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