Acetic Acid → HCID 21959504, compound

HRID 238515Notes

Reaction equation

HRID 238515 reaction equation
[CH3:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.CC(O)=O>C1COCC1.[Zn]>[CH3:11][C:2]([C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)([CH3:1])[CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22249395HCID 22249395, compound

Product 1

HCID 21959504HCID 21959504, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[3-methyl-3-(4-nitro-phenyl)-butyl]-morpholine (0.50 g, 1.8 mmol, Step E) in THF (40 mL) was added AcOH (1.97 mmol, 34.5 mmol) followed by zinc (9.1 g, 137 mmol). The mixture was stirred for 1 h and filtered on Celite®. The mixture was diluted with H2O, and aqueous NaHCO3 and the THF was evaporated. The residue was extracted with EtOAc, dried and evaporated to give the title intermediate. Calc'd for C15H24N2O: 248.19.

Workup

  1. filtrationfiltered on Celite®
  2. additionThe mixture was diluted with H2O, and aqueous NaHCO3
  3. customthe THF was evaporated
  4. extractionThe residue was extracted with EtOAc
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-f353277955fa4637ac9faa8cfd2232df
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

Loading…