Acryloyl chloride → HCID 59441931, compound

HRID 1014325Notes

Reaction equation

HRID 1014325 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH2:7][CH2:6]2.C(N(C(C)C)CC)(C)C.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26].[CH:29]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)([CH3:31])[CH3:30]>ClCCl.C(O)C>[CH3:30][CH:29]([N:32]1[CH2:37][CH2:36][N:35]([CH2:26][CH2:25][C:24]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=3)[CH2:6][CH2:7]2)=[O:27])[CH2:34][CH2:33]1)[CH3:31]

Participants

7

Reactant 4

HCID 13140Acryloyl chlorideHCID 780131-IsopropylpiperazineHCID 81531DiisopropylethylamineHCID 594416565-methoxy-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 59441931HCID 59441931, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (1.0 g, 5.15 mmol) and polymer-bound diisopropyl ethylamine (4.20 g, 15.46 mmol) in dichloromethane (200 mL) was added acryloyl chloride (0.51 g, 5.67 mmol) via a dropwise addition. After stirring overnight at rt, the solids were removed by vacuum filtration and washed with dichloromethane. The filtrate was concentrated under reduced pressure and maintained under vacuum for several hours. A portion of this crude mixture (0.52 g, 2.1 mmol) was redissolved in absolute ethanol (25 mL) and to this was added isopropylpiperazine (0.81 g, 6.29 mmol). After heating at 60° C. for 3 hrs, the reaction was concentrated under reduced pressure and solids were recrystallized from ethyl acetate/hexanes to provide 1-{3-[4-(1-methylethyl)-1-piperazinyl]propanoyl}-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (0.62 g, 79%). ESIMS (M+H)+=377.

Workup

  1. additionvia a dropwise addition
  2. customthe solids were removed by vacuum filtration
  3. washwashed with dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. temperaturemaintained under vacuum for several hours
  6. temperatureAfter heating at 60° C. for 3 hrs
  7. concentrationthe reaction was concentrated under reduced pressure and solids
  8. customwere recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-876998f8301c40db8781e2246cab6f0a
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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