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Dibenz(b,f)azepine → (Z)-2-(5H-dibenzo[b,f]azepin-5-yl)acetonitrile

HRID 718082
Notes
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Reaction equation

HRID 718082 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.S([O-])([O-])(=O)=O.[CH2:21]([N+:25](CCCC)(CCCC)CCCC)[CH2:22]CC.C([N+](CCCC)(CCCC)CCCC)CCC.BrCC#N.[OH-].[Na+]>C(Cl)Cl.O>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]([CH2:22][C:21]#[N:25])[C:5]=2[CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 9212Dibenz(b,f)azepineHCID 11534BromoacetonitrileHCID 14798Sodium HydroxideHCID 11433187Bis(tetrabutylammonium) sulphate

Product 1

HCID 11345294(Z)-2-(5H-dibenzo[b,f]azepin-5-yl)acetonitrileYield 51.7%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

(Z)-5H-dibenzo[b,f]azepine (0.1 g, 0.5 mmol), tetrabutylammonium sulfate (0.35 g, 1.0 mmol), 2-bromoacetonitrile (0.4 mL, 5.0 mmol) and 50% aqueous sodium hydroxide (1 mL) were mixed in DCM (1 mL) and the reaction mixture was stirred for 5 days. The mixture was diluted in water and the aqueous layer was extracted with DCM (2 times). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (0% to 50% ethyl acetate in hexanes) to afford title compound 365 (60 mg, 50%). 1H NMR (CDCl3) δ (ppm): 7.36-7.31 (m, 2H), 7.26-7.23 (m, 2H), 7.17-7.11 (m, 4H), 6.76 (s, 2H), 4.47 (s, 2H).

Workup

  1. extractionthe aqueous layer was extracted with DCM (2 times)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (0% to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4b2c20dccdb047869b6e8d496f3d08b3
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193749B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes