Morpholine → HCID 86699689, compound

HRID 1487217Notes

Reaction equation

HRID 1487217 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.C(=O)([O-])[O-].[K+].[K+].[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C=O)C.O>[N+:14]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[CH:7]=[CH:6][N:5]2[CH2:4][CH2:3][CH2:2][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 86699688HCID 86699688, compound

Product 1

HCID 86699689HCID 86699689, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(3-bromopropyl)-4-nitro-1H-indole (8.18 g, 28.9 mmol) in anhydrous N,N′-dimethylformamide (200 mL) was added grounded potassium carbonate (12 g, 87 mmol) in portions. Then a solution of morpholine (12.6 g, 144.8 mmol) in N,N′-dimethylformamide was added dropwise. The mixture was stirred at 80° C. for 12 hours, diluted with water and extracted with ethyl acetate. The organic phases were combined, washed by brine, dried over anhydrous sodium sulfate, filtrated and evaporated to afford the product 4-(3-(4-nitro-1H-indol-1-yl)propyl)morpholine, which was used for the next step without purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed by brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-3f2ea4dd0b0a4bc4b830750975df4144
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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