Dimethylformamide → N-Methyl-4-phenylpiperidine-4-carboxamide

HRID 1586114Notes

Reaction equation

HRID 1586114 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.[CH3:38][N:39]([CH:41]=[O:42])C>C(Cl)Cl>[CH3:38][NH:39][C:41]([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:42]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6364545Methylamine hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.98 g of triethylamine are added to a solution of 1.5 g of the compound obtained in the preceding stage in 5 ml of DCM and 5 ml of DMF, followed by 0.49 g of methylamine hydrochloride. The mixture is cooled on an ice bath, 2.39 g of BOP are added and the mixture is kept stirring for 24 hours while allowing the temperature to rise to RT. The reaction mixture is concentrated under vacuum, the residue extracted with ether, washed with water, with a buffer solution pH=2, with water, with a 10% solution of NaOH, with water, with a saturated solution of NaCl, dried over MgSO4 and evaporated under vacuum. 1.4 g of the expected product are obtained.

Workup

  1. temperatureThe mixture is cooled on an ice bath
  2. customto rise to RT
  3. concentrationThe reaction mixture is concentrated under vacuum
  4. extractionthe residue extracted with ether
  5. washwashed with water, with a buffer solution pH=2, with water, with a 10% solution of NaOH, with water, with a saturated solution of NaCl
  6. dry with materialdried over MgSO4
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-a07bb1ab5f814652b6fc35e7b00e53e1
Source dataset
uspto-grants-1999_08
Patent number
US05942523

Reaction notes

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