Morpholine → HCID 66632582, compound

HRID 659165Notes

Reaction equation

HRID 659165 reaction equation
Br[CH2:2][C:3]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[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[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:4]=2[C:5]#[N:6])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 666328472-(Bromomethyl)-3-nitrobenzonitrile

Product 1

HCID 66632582HCID 66632582, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(bromomethyl)-3-nitrobenzonitrile (1.10 g, 4.56 mmol) and morpholine (0.80 g, 9.13 mmol) in CH2Cl2 (15 mL) was added triethylamine (1.85 g, 18.25 mmol) dropwise at 0° C. The mixture was stirred at room temperature for 1.5 h and evaporated to dryness under reduced pressure. The residue was diluted with water (10 mL) and extracted with CH2Cl2 (3×50 mL). The CH2Cl2 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 2-(morpholinomethyl)-3-nitrobenzonitrile (1.02 g, 90%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.90 (br d, 1H, J=8.0 Hz), 7.84 (dd, 1H, J=8.0, 1.2 Hz), 7.56 (t, 1H, J=8.0 Hz), 3.99 (s, 2H), 3.60 (br t, 4H, J=4.4 Hz), 2.46 (br s, 4H).

Workup

  1. customevaporated to dryness under reduced pressure
  2. additionThe residue was diluted with water (10 mL)
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe CH2Cl2 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-db8ac8174c1a4d9396b7024fed02527b
Source dataset
uspto-grants-2011_12
Patent number
US08080568B1

Reaction notes

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