Trifluoroacetic acid → 8,8-dimethyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline

HRID 1754543Notes

Reaction equation

HRID 1754543 reaction equation
[CH3:1][C:2]1([CH3:23])[C:11]2[C:6]3=[C:7]([CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][CH2:15][N:5]3[CH2:4][CH2:3]1)[CH:8]=[CH:9][CH:10]=2.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1([CH3:23])[C:11]2[C:6]3=[C:7]([CH2:12][NH:13][CH2:14][CH2:15][N:5]3[CH2:4][CH2:3]1)[CH:8]=[CH:9][CH:10]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712749tert-butyl 8,8-dimethyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate

Product 1

HCID 867127508,8-dimethyl-2,3,4,6,7,8-hexahydro-1H-[1,4]diazepino[6,7,1-ij]quinolineYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

287 mg (0.9 mmol) of tert-butyl 8,8-dimethyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate of step 1.3 were dissolved in 5 mL of dichloromethane and treated with 2.5 mL of trifluoroacetic acid. The mixture was stirred over night at room temperature and then extracted once with water (10 mL). The organic phase was then extracted twice with a diluted solution of sodium hydroxide (10 mL each), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica (eluent: 10-30% methanol in dichloromethane) to yield 141 mg of the title compound as a yellow oil.

Workup

  1. extractionextracted once with water (10 mL)
  2. extractionThe organic phase was then extracted twice with a diluted solution of sodium hydroxide (10 mL each)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica (eluent: 10-30% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8bca3089d6ad403d9d1f117b8484048e
Source dataset
uspto-grants-2015_10
Patent number
US09169253B2

Reaction notes

Loading…