Water → 4-(4-Benzyl-[1,4]oxazepan-6-yl)-benzonitrile

HRID 515471Notes

Reaction equation

HRID 515471 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[CH2:12][O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O.[CH3:29][N:30]1CCCC1=O>[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.O.O.O.[K+].[K+].[K+].[K+].[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[CH2:1]([N:8]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([C:29]#[N:30])=[CH:17][CH:16]=2)[CH2:12][O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 667185934-Benzyl-6-(4-bromo-phenyl)-[1,4]oxazepane

Product 1

HCID 667184644-(4-Benzyl-[1,4]oxazepan-6-yl)-benzonitrileYield 79%

Reagents, catalysts & solvents 3

HCID 161067Potassium ferrocyanide trihydrateCatalystHCID 167845palladium(II) acetateCatalystHCID 15826098Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+)Catalyst

Conditions

Temperature
120 °C

Procedure

A mixture of 4-benzyl-6-(4-bromo-phenyl)-[1,4]oxazepane (2.4 g, 6.9 mmol), potassium hexacyanoferrate(II) trihydrate (1.48 g, 3.5 mmol), palladium(II) acetate (1.6 mg, 0.007 mmol), diphenylphosphinoferrocene (7.8 mg, 0.014 mmol) and sodium carbonate (0.74 g, 7.0 mmol) in N-methylpyrrolidone (NMP) (7 mL) was prepared in a round bottom flask at room temperature under nitrogen atmosphere and the mixture was heated to 120° C. After stirring for 10 hours, the reaction mixture was cooled to room temperature and poured into water. The organic materials were extracted with ethyl acetate and wash with brine. The organic layer was separated and dried over anhydrous sodium sulfate. After concentration, the residual oil was passed through flash column chromatography on silica gel (hexane/ethyl acetate=90/10 to 50/50 as an eluant) to obtain pure 4-(4-benzyl-[1,4]oxazepan-6-yl)-benzonitrile (1.6 g, 5.5 mmol, 79%) as light yellow oil.

Workup

  1. customwas prepared in a round bottom flask at room temperature under nitrogen atmosphere
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionThe organic materials were extracted with ethyl acetate
  4. washwash with brine
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationAfter concentration

Sources & evidence

ORD record
ord-72baefa755f9490182f1e5ccffd16f2f
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

Loading…