Morpholine → HCID 59441669, compound

HRID 1014319Notes

Reaction equation

HRID 1014319 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.Br[CH2:25][C:26](Cl)=[O:27].C(=O)([O-])[O-].[K+].[K+].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>ClCCl>[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])[N:8]([C:26](=[O:27])[CH2:25][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)[CH2:7][CH2:6]2

Participants

7

Reactant 5

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chlorideHCID 594416565-methoxy-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 59441669HCID 59441669, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (0.5 g, 2.57 mmols) and polymer-bound diisopropyl ethylamine (2.10 g, 7.73 mmol) in dichloromethane (50 mL) was added bromoacetyl chloride (0.49 g, 3.11 mmol) via a dropwise addition. After stirring for 2 hrs at room temperature the solids were removed by vacuum filtration. The filtrate was concentrated under reduced pressure, maintained under high vacuum for several hours, redissolved in THF (20 mL) and to this crude mixture was added potassium carbonate (1.06 g, 7.68 mmols), catalytic Kl, and morpholine (0.67 g, 7.68 mmols). After overnight stirring, the reaction was diluted with dichloromethane (50 mL), washed with water (25 mL), filtered through a cotton plug and concentrated by rotary evaporation to provide 5-(methyloxy)-1-(4-morpholinylacetyl)-6-nitro-2,3-dihydro-1H-indole (0.56 g, 67% over two steps). ESIMS (M+H)+=322.

Workup

  1. additionvia a dropwise addition
  2. customwere removed by vacuum filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. temperaturemaintained under high vacuum for several hours
  5. dissolutionredissolved in THF (20 mL) and to this crude mixture
  6. stirringAfter overnight stirring
  7. washwashed with water (25 mL)
  8. filtrationfiltered through a cotton plug
  9. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-8ffc5bb726324b8890ed61427ded5b16
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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