Morpholine → HCID 66632633, compound

HRID 659166Notes

Reaction equation

HRID 659166 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:6]#[N:7].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[O:17]1[CH2:18][CH2:19][N:14]([CH2:2][C:3]2[CH:4]=[C:5]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=2)[C:6]#[N:7])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 14567863HCID 14567863, compound

Product 1

HCID 66632633HCID 66632633, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(bromomethyl)-5-nitrobenzonitrile (1.50 g, 6.22 mmol) and morpholine (0.65 g, 7.46 mmol) in CH2Cl2 (15 mL) was added triethylamine (1.88 g, 18.66 mmol) dropwise at 0° C. The mixture was stirred at room temperature overnight and then evaporated to dryness under reduced pressure. The residue was diluted with water (15 mL) and extracted with EtOAc (3×50 mL). The EtOAc solution was dried over anhydrous Na2SO4, filtered and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of EtOAc and hexane as eluent to give 3-(morpholinomethyl)-5-nitrobenzonitrile (0.87 g, 85%) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.45 (br s, 1 H), 8.41 (br s, 1H), 8.01 (br s, 1H), 3.74 (br t, 4H, J=4.4 Hz), 3.64 (s, 2H), 2.48 (br t, 4H, J=4.4 Hz).

Workup

  1. customevaporated to dryness under reduced pressure
  2. additionThe residue was diluted with water (15 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe EtOAc solution was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by MPLC on silica gel using
  8. additiona mixture of EtOAc and hexane as eluent

Sources & evidence

ORD record
ord-7037359605ff41b4a67a15da98134b8f
Source dataset
uspto-grants-2011_12
Patent number
US08080568B1

Reaction notes

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