Sodium Cyanide → 1-(7-Cyano-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl)ethanone

HRID 1668600Notes

Reaction equation

HRID 1668600 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:19]=[CH:18][C:9]2[CH2:10][CH2:11][N:12]([C:15](=[O:17])[CH3:16])[CH2:13][CH2:14][C:8]=2[CH:7]=1.[C:20]([Cu])#[N:21].[C-]#N.[Na+]>OS(O)(=O)=O.O>[C:20]([C:6]1[CH:19]=[CH:18][C:9]2[CH2:10][CH2:11][N:12]([C:15](=[O:17])[CH3:16])[CH2:13][CH2:14][C:8]=2[CH:7]=1)#[N:21]

Participants

7

Reactant 4

HCID 8929Sodium CyanideHCID 21822924HCID 21822924, compoundHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 673587901-(7-Cyano-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl)ethanoneYield 63.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

NaNO2 (0.53 g, 1.05 eq) was added portion wise to a solution of 1-(7-amino-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl)ethanone (1.5 g, 1 eq) in 1.5 M H2SO4 (10 mL) maintained to 0° C. The obtained solution was added drop wise to a solution of CuCN (0.8 g, 1.23 eq) and NaCN (1.25 g, 3.42 eq) in H2O (5 ml), then the reaction mixture was allowed to warm to room temperature and extracted with ethyl acetate. The organic solution was washed with 5% aqueous NaHCO3 and brine, then dried over Na2SO4 and concentrated to afford a crude material (1.5 g). Chromatography over silica gel (ethyl acetate/MeOH: 9/1) yielded the title compound as a pale orange solid (1.0 g, 63% yield).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic solution was washed with 5% aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto afford a crude material (1.5 g)

Sources & evidence

ORD record
ord-052a2d10984e4eebb13255e3826dd77e
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

Loading…