Dichloromethane → 4-(Azepan-4-yl)benzonitrile

HRID 541217Notes

Reaction equation

HRID 541217 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].C(Cl)Cl.FC(F)(F)C(O)=O>C(OCC)(=O)C>[NH:12]1[CH2:13][CH2:14][CH2:15][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68288974Tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate2×

Product 1

HCID 682889074-(Azepan-4-yl)benzonitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a vial containing tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate (compound 40.3, 77 mg, 0.257 mmol, 1.0 equiv) was added DCM (500 μL) and trifluoroacetic acid (198 μL, 2.57 mmol, 10 equiv) and the mixture was stirred vented for 90 min. The mixture was diluted into ethyl acetate (5 mL) and washed with saturated sodium bicarbonate (5 mL). The aqueous was adjusted to pH 10-11 and extracted with addition ethyl acetate until no product remained. The combined organics were dried (Na2SO4), filtered and concentrated to obtain the title compound as a yellow oil (51 mg, theoretical). m/z (ES+) 201 (M+H)+.

Workup

  1. washwashed with saturated sodium bicarbonate (5 mL)
  2. extractionextracted with addition ethyl acetate until no product
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d21c4ea4cfb4407e8225741c5872002f
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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