4-Methylmorpholine → N-methoxy-N-methyl-2-propylamino-4-trifluoromethyl-benzamide

HRID 1042445Notes

Reaction equation

HRID 1042445 reaction equation
[CH2:1]([NH:4][C:5]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])[CH2:2][CH3:3].[CH3:18][NH:19][O:20][CH3:21].CN1CCOCC1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C(Cl)Cl>[CH3:21][O:20][N:19]([CH3:18])[C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:12]([C:14]([F:17])([F:16])[F:15])=[CH:13][C:5]=1[NH:4][CH2:1][CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 668556182-Propylamino-4-(trifluoromethyl)benzoic acid

Product 1

HCID 86649954N-methoxy-N-methyl-2-propylamino-4-trifluoromethyl-benzamideYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Propylamino-4-(trifluoromethyl)benzoic acid (147 mg, 0.594 mmol) in CH2Cl2 was reacted with N,O-dimethylhydroxy amine (82 mg), NMM (0.2 ml) and DMTMM (222 mg) at room temperature overnight. The reaction mixture was quenched by adding H2O (3 ml). The reaction solvent was removed under reduced pressure. Water (30 ml) was added to the resulting residue, which was extracted with ethylacetate (30 ml×3). The combined organic layer was washed with sat. NaHCO3 solution (30 ml), 1N HCl aqueous solution (30 ml) and brine (30 ml), and then dried over MgSO4. The filterate was concentrated in vacuo. The residue was purified with column chromatography to yield the title compound (98 mg, 57%).

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding H2O (3 ml)
  3. customThe reaction solvent was removed under reduced pressure
  4. additionWater (30 ml) was added to the resulting residue, which
  5. extractionwas extracted with ethylacetate (30 ml×3)
  6. washThe combined organic layer was washed with sat. NaHCO3 solution (30 ml), 1N HCl aqueous solution (30 ml) and brine (30 ml)
  7. dry with materialdried over MgSO4
  8. concentrationThe filterate was concentrated in vacuo
  9. customThe residue was purified with column chromatography

Sources & evidence

ORD record
ord-27f52a2ac0454ec19f032603d79107da
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

Loading…