Morpholine → HCID 21955010, compound

HRID 2095111Notes

Reaction equation

HRID 2095111 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([NH2:12])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1.C(N(CC)CC)C.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>C1COCC1>[N:20]1([CH2:2][C:3]2[CH:4]=[C:5]([NH2:12])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 21955038HCID 21955038, compound

Product 1

HCID 21955010HCID 21955010, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromomethyl-5-nitrophenylamine (398 mg, 1.72 mmol), triethylamine (0.3 mL) and morpholine (0.2 mL) in 15 mL of THF was heated at 60° C. for 30 minutes. The solvent was evaporated in vacuo. The residue was mixed with water (20 mL) and extracted with ether. Organic layer was separated, dried over MgSO4 and concentrated in vacuo to afford a yellow solid (411 mg), which was purified by column chromatography. The title compound was isolated as yellow crystals in an amount of 302 mg (1.274 mmol, 74%); MS (m/z, ES+): 238 (M+1, 100%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionThe residue was mixed with water (20 mL)
  3. extractionextracted with ether
  4. customOrganic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f5cc86be5004576985c213553c9810c
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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