Ammonia → HCID 23447614, compound

HRID 1840601Notes

Reaction equation

HRID 1840601 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C:14]2=[O:26])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH3:27][N:28](C=O)C.C(OCC)(=O)C.N>[C-]#N.[Zn+2].[C-]#N.O>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][N:13]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:27]#[N:28])=[CH:3][CH:4]=2)[C:9]([O:11][CH3:12])=[O:10])[C:14](=[O:26])[CH2:15]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 23447536HCID 23447536, compound

Product 1

HCID 23447614HCID 23447614, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-(4-bromophenyl)-2-[4-(tert-butoxycarbonyl)-2-oxo-1-piperazinyl]acetate (1.28 g), zinc cyanide (211 mg), tetrakis (triphenylphosphine)palladium (139 mg) and DMF (10 ml) was stirred at 80° C. for 6 hours and cooled. To the reaction solution were added ethyl acetate, water and a little amount of ammonia solution. The organic layer was separated, washed with saturated brine, dried and concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1) to give yellow syrup of methyl 2-[4-(tert-butoxycarbonyl)-2-oxo-1-piperazinyl]-2-(4-cyanophenyl)acetate (1.01 g).

Workup

  1. temperaturecooled
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-2d1b8a29277b4a888d484ec1c2fdd755
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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