3-(4-Fluorobenzoyl)propyl chloride → 4-(1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indol-9-yl)-1-(4-fluorophenyl)-1-butanone

HRID 51059Notes

Reaction equation

HRID 51059 reaction equation
[CH2:1]1[N:11]2[C:12]3[C:8]([CH:9]4[CH2:17][CH2:16][NH:15][CH2:14][CH2:13][CH:10]42)=[CH:7][CH:6]=[CH:5][C:4]=3[O:3][CH2:2]1.Cl[CH2:19][CH2:20][CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:23].CCN(C(C)C)C(C)C>O1CCOCC1>[CH2:1]1[N:11]2[C:12]3[C:8]([CH:9]4[CH2:17][CH2:16][N:15]([CH2:19][CH2:20][CH2:21][C:22]([C:24]5[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=5)=[O:23])[CH2:14][CH2:13][CH:10]42)=[CH:7][CH:6]=[CH:5][C:4]=3[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 81531DiisopropylethylamineHCID 227357541,2,7,8,9,10,11,11a-octahydro-6bH-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole

Product 1

HCID 227354474-(1,2,6b,7,8,10,11,11a-octahydro-9H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indol-9-yl)-1-(4-fluorophenyl)-1-butanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,2,7,8,9,10,11,11a-octahydro-6bH-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole (97.8 mg, 0.42 mmol), 4-chloro-1-(4-fluorophenyl)-1-butanone (172 mg, 0.86 mmol), KI (71.2 mg, 0.43 mmol), and DIEA (550 mg, 4.3 mmol) were suspended in dioxane (2 mL). The reaction mixture was refluxed for 18 hrs. After cooling to rt, the solution was concentrated. The residue was immediately purified by column chromatography to afford the title compound. MS-ESI: 395[MH]+.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hrs
  2. concentrationthe solution was concentrated
  3. customThe residue was immediately purified by column chromatography

Sources & evidence

ORD record
ord-fa0fa3fb99584f6fb537c69f742d1b39
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

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