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

HRID 1955049Notes

Reaction equation

HRID 1955049 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-165f6a03ef1a47b88e218df6747c418b
Source dataset
uspto-grants-2000_09
Patent number
US06124316

Reaction notes

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