4-Methylmorpholine → HCID 86649956, compound

HRID 1042450Notes

Reaction equation

HRID 1042450 reaction equation
[CH2:1]([O: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]([OH:9])=O)[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-]>C1COCC1>[CH3:21][O:20][N:19]([CH3:18])[C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:12]([C:14]([F:17])([F:16])[F:15])=[CH:13][C:5]=1[O: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 224941922-Propoxy-4-(trifluoromethyl)benzoic acid

Product 1

HCID 86649956HCID 86649956, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Propoxy-4-(trifluoromethyl)benzoic acid (457 mg, 1.93 mmol) in THF was reacted with N,O-dimethylhydroxy amine (378 mg), NMM (0.65 ml) and DMTMM (947 mg) at room temperature overnight. The reaction solvent was removed in vacuo. Water (30 ml) was added to the resulting residue, which was extracted with ethyl acetate (30 ml×3). The combined organic layer was washed with 1 M NaHCO3 (30 ml), 1N HCl (30 ml) and brine (30 ml) and dried over MgSO4. The filterate was purified with column chromatography (Hex/EtOAc=4/1) to yield the title compound (277 mg, 49%).

Workup

  1. customThe reaction solvent was removed in vacuo
  2. additionWater (30 ml) was added to the resulting residue, which
  3. extractionwas extracted with ethyl acetate (30 ml×3)
  4. washThe combined organic layer was washed with 1 M NaHCO3 (30 ml), 1N HCl (30 ml) and brine (30 ml)
  5. dry with materialdried over MgSO4
  6. customThe filterate was purified with column chromatography (Hex/EtOAc=4/1)

Sources & evidence

ORD record
ord-5987c93a87ff4f308489e1355f8dac77
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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