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Dimethylformamide → HCID 22248286, compound

HRID 890113
Notes
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Reaction equation

HRID 890113 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[C:23]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:22][CH:21]=[CH:20][N:19]=2)[CH2:13][CH2:12]1)=[O:10].[OH-].[Na+].C(OCC)(=O)C.[CH3:37][N:38](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]([O:24][C:23]1[C:18]([CH2:17][N:14]2[CH2:15][CH2:16][CH:11]([C:9](=[O:10])[CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[C:37]#[N:38])[CH2:12][CH2:13]2)=[N:19][CH:20]=[CH:21][N:22]=1)([CH3:28])([CH3:27])[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 22248057HCID 22248057, compound

Product 1

HCID 22248286HCID 22248286, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 11186
Zinc cyanide (Zn(CN)2)
Catalyst
HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

After dissolving 298 mg of 2-(2-bromophenyl)-1-[1-(3-tert-butoxy-2-pyrazinylmethyl)piperidin-4-yl]ethanone in 2 ml of N,N-dimethylformamide, 235 mg of zinc cyanide and 77 mg of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was stirred overnight at 100° C. A 1N sodium hydroxide solution was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (90 mg, 34% yield).

Workup

  1. additionwere added
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c1aeeeb85624441abf2803a5af02e6a5
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06995144B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes