Trifluoroacetic acid → 2,3,4,5-Tetrahydro-1H-3-benzazepine-7-carbonitrile

HRID 33200Notes

Reaction equation

HRID 33200 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([C:19]#[N:20])=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:19]([C:17]1[CH:16]=[CH:15][C:12]2[CH2:13][CH2:14][NH:8][CH2:9][CH2:10][C:11]=2[CH:18]=1)#[N:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18173275tert-Butyl 7-cyano-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate

Product 1

HCID 181732792,3,4,5-Tetrahydro-1H-3-benzazepine-7-carbonitrileYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(tert-butyloxycarbonyl)-7-cyano-2,3,4,5-tetrahydro-1H-3-benzazepine (765 mg, 2.81 mmol) and trifluoroacetic acid (2 ml), in dichloromethane (20 ml) was stirred at 40° C. for 1 h. The reaction mixture was evaporated to dryness in vacuo and partitioned between ethyl acetate (50 ml) and water (50 ml). The aqueous layer was basified using potassium carbonate and re-extracted with ethyl acetate (2×30 ml). The combined basic organic extracts were dried over sodium sulfate and evaporated in vacuo to give the title compound as a colourless oil (212 mg, 44%).

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. custompartitioned between ethyl acetate (50 ml) and water (50 ml)
  3. extractionre-extracted with ethyl acetate (2×30 ml)
  4. dry with materialThe combined basic organic extracts were dried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3680548be0b54ada8f1c647f6c494cc6
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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