Dimethylformamide → 2-(4-chlorophenyl)-N-cyclohexyl-2-methylpropanamide

HRID 2247308Notes

Reaction equation

HRID 2247308 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([CH3:40])([CH3:39])[C:36](O)=[O:37])=[CH:31][CH:30]=1.CN1CCOCC1.C1(N)CCCCC1.CN(C=O)C.C(O)(C(F)(F)F)=O>CS(C)=O>[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]([CH3:40])([CH3:39])[C:36]([NH:8][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:11]2)=[O:37])=[CH:33][CH:34]=1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 7965CyclohexylamineHCID 79724-MethylmorpholineHCID 804062-(4-Chlorophenyl)-2-methylpropionic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 116591682-(4-chlorophenyl)-N-cyclohexyl-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

BOP (200 μL, 0.25 M in DMF, 50 μmol) was added to a solution of 2-(4-chlorophenyl)-2-methylpropanoic acid (200 μL, 0.25 M in DMF, 50 μmol) at RT, followed by addition of N-methyl morpholine (40 μL). The mixture was stirred at RT for 15 min, then a solution of cyclohexylamine in DMF (200 μL, 0.25 M in DMF, 50 μmol) was added. The resulting mixture was stirred at RT for 3 h, and then was adjusted by TFA to PH=2.0, and diluted with DMSO (1100 μL). The resulting solution was purified by prep.-HPLC to afford the desired product 2-(4-chlorophenyl)-N-cyclohexyl-2-methylpropanamide. LCMS: (M+H)+=280.0/282.0.

Workup

  1. stirringThe resulting mixture was stirred at RT for 3 h
  2. customThe resulting solution was purified by prep.-HPLC

Sources & evidence

ORD record
ord-f026db2a1f324d42994612dd26791d0c
Source dataset
uspto-grants-2010_03
Patent number
US07687665B2

Reaction notes

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