Acetic Acid → HCID 21959504, compound

HRID 557369Notes

Reaction equation

HRID 557369 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-6cdeedf7b8744d78800252dcafa24855
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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