2-Bromobenzonitrile → HCID 67416808, compound

HRID 1667527Notes

Reaction equation

HRID 1667527 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][C@H:11]1[CH2:16][NH:15][CH2:14][CH2:13][NH:12]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>CC(N(C)C)=O.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:10][C@H:11]1[NH:12][CH2:13][CH2:14][N:15]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:16]1

Participants

8

Reactant 4

HCID 162722-BromobenzonitrileHCID 634876Binap, (A+-)-HCID 27342192-Methylpiperazine, (S)-HCID 23676156Sodium t-butoxide

Product 1

HCID 67416808HCID 67416808, compoundYield 48.8%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture 2-bromobenzonitrile (1.0 g, 5.494 mmol), (S)-(+)-2-methylpiperazine (0.60 g, 5.99 mmol), Pd2(dba)3 (0.503 g, 0.549 mmol), rac-BINAP (1.026 g, 1.648 mmol) and NaOtBu (2.11 g, 21.976 mmol) in DMA (27 mL) was heated at 80° C. for 2.5 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography (EtOAc/MeOH) afforded 2-((R)-3-methyl-piperazin-1-yl)-benzonitrile (540 mg) as a white solid. 1H (400 MHz, d6-DMSO) δ: ppm; m/z (M+1) 202.21.

Workup

  1. temperatureto cool
  2. washwashed with water
  3. washThe organic layer was washed with sat.aq
  4. dry with materialNaHCO3, brine and dried (Na2SO4)

Sources & evidence

ORD record
ord-f6cff52468254721b2b64d6bf34709b7
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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