Triethylamine → (3,4-Dihydro-2H-benzo[1,4]oxazin-3-yl-methyl)-[3-(5-fluoro-1H-indol-3-yl)propyl]-amine

HRID 427270Notes

Reaction equation

HRID 427270 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O.[NH2:25][CH2:26][C:27]1[CH2:28][O:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1.C(N(CC)CC)C>C(#N)C>[O:29]1[C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[NH:32][CH:27]([CH2:26][NH:25][CH2:13][CH2:12][CH2:11][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][CH:6]=2)[CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 150205425-Fluoro-3-(3-p-toluenesulfonyloxypropyl)indoleHCID 539412263-Aminomethyl-1,4-benzoxazine

Product 1

HCID 9945844(3,4-Dihydro-2H-benzo[1,4]oxazin-3-yl-methyl)-[3-(5-fluoro-1H-indol-3-yl)propyl]-amineYield 52.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-fluoro-3-(3-p-toluenesulfonyloxypropyl)indole (0.52 g, 1.5 mmol) and 3-aminomethyl-1,4-benzoxazine (0.25 g, 1.5 mmol) [prepared in accordance with the procedure set forth in Ind. J. Chem., 13:462-467 (1975)] in acetonitrile (15 mL) was added triethylamine (0.42 mL, 3.0 mmol) at room temperature. The reaction mixture was allowed to reflux 18 h, cooled and concentrated. The crude product was purified by silica gel column chromatography (ethyl acetate/methanol/NH4OH, 98/2/0.5) to afford 265 mg (52%) of the free base.

Workup

  1. temperatureto reflux 18 h
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column chromatography (ethyl acetate/methanol/NH4OH, 98/2/0.5)

Sources & evidence

ORD record
ord-fc7db05ae6904bb39a188413da364d05
Source dataset
uspto-grants-2001_11
Patent number
US06313114B1

Reaction notes

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