Triethylamine → N-Methyl-4-phenylpiperidine-4-carboxamide

HRID 1585738Notes

Reaction equation

HRID 1585738 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.Cl.[CH3:9]N.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2N=N1.C(Cl)Cl.[CH3:41][N:42]([CH:44]=[O:45])C>>[CH3:41][NH:42][C:44]([C:9]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:5][CH2:4][NH:3][CH2:6][CH2:7]1)=[O:45]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6364545Methylamine hydrochlorideHCID 22350042dichloromethane N,N-dimethylformamide

Product 1

HCID 22741819N-Methyl-4-phenylpiperidine-4-carboxamide

Conditions

Temperature
2.5 °C

Procedure

5.29 g of triethylamine and then 1.32 g of methylamine hydrochloride are added to a solution of 4 g of the compound obtained in step A of PREPARATION 1.5 in 20 ml of a DCM/DMF (50:50; v/v) mixture, the resulting mixture is cooled to 0-5° C., 6.37 g of BOP are added and the reaction mixture is left stirring for 24 hours at RT. It is concentrated under vacuum, the residue is extracted with ether, the organic phase is washed with water, with a pH 2 buffer solution, with water, with 10% NaOH solution, with water and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. 3.72 g of the expected product are obtained.

Workup

  1. waitthe reaction mixture is left
  2. concentrationIt is concentrated under vacuum
  3. extractionthe residue is extracted with ether
  4. washthe organic phase is washed with water, with a pH 2 buffer solution, with water, with 10% NaOH solution, with water and with saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-b7fb7914e9504580a297b616e013f918
Source dataset
uspto-grants-1999_08
Patent number
US05939411

Reaction notes

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