p-Aminoacetophenone → HCID 17539973, compound

HRID 351633Notes

Reaction equation

HRID 351633 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7468p-AminoacetophenoneHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 17539973HCID 17539973, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of piperidine-1,4-dicarboxylic acid 1-tert-butyl ester (1.69 g, 7.4 mmol) in DMF (20 ml) was added 1-(4-aminophenyl)ethanone (1 g, 7.4 mmol), NEM (0.852 g, 7.4 mmol) and TOTU (2.427 g, 7.4 mmol). The solution was stirred for 16 h at room temperature. The solvent was removed and the residue was dissolved in ethyl acetate (50 ml) and washed with saturated aqueous NaHCO3 solution (5 ml) and HCl (1 N, 10 ml). The organic phase was dried (MgSO4) and filtered. The solvent was removed to give 1.344 g (52%) of the title compound.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  3. washwashed with saturated aqueous NaHCO3 solution (5 ml) and HCl (1 N, 10 ml)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-278827d43150445bbaf3ca98d6947ed9
Source dataset
uspto-grants-2004_06
Patent number
US06743790B2

Reaction notes

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