Dichloromethane → 3-(5-Morpholin-4-yl-2-nitro-phenoxy)-propionitrile

HRID 1041652Notes

Reaction equation

HRID 1041652 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15].C(Cl)Cl>CS(C)=O.CCOCC.O>[N:17]1([C:10]2[CH:11]=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[C:8]([CH:9]=2)[O:7][CH2:6][CH2:5][C:1]#[N:2])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 8929Sodium CyanideHCID 672636974-[3-(2-Bromo-ethoxy)-4-nitro-phenyl]-morpholine

Product 1

HCID 672634833-(5-Morpholin-4-yl-2-nitro-phenoxy)-propionitrileYield 57%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium cyanide (79 mg, 1.6 mmol) was added to 4-[3-(2-Bromo-ethoxy)-4-nitro-phenyl]-morpholine (447 mg, 1.35 mmol) in Dimethyl sulfoxide (5 mL) and the reaction was stirred at room temperature 48 h. The mixture was diluted with 50 mL Et2O and 20 mL water. DCM was added to solubilize ppt. The layers were separated and the aq. extracted 3×50 mL DCM. The combined organic extracts were washed with satd. sodium bicarbonate (50 mL) and brine (50 mL), conc. in vacuo and taken up in DCM for application to a 25 g SiO2 pre-load cartridge. Chromatography (0-100% EtOAc:Hex) afforded 3-(5-Morpholin-4-yl-2-nitro-phenoxy)-propionitrile as a yellow solid (212 mg, 57%). 1H-NMR (CDCl3): 8.01 (d, 1H, J=9.2 Hz), 6.52 (d, 1H, J=9.2 Hz), 6.40 (s, 1H), 4.31 (t, 2H, J=7.0 Hz), 3.86 (t, 4H, J=4.6 Hz), 3.35 (t, 4H, J=4.6 Hz), 2.93 (t, 2H, J=7.0 Hz).

Workup

  1. customThe layers were separated
  2. extractionthe aq. extracted 3×50 mL DCM
  3. washThe combined organic extracts were washed with satd

Sources & evidence

ORD record
ord-cae0d73f5cbe4020be6c0718322618dd
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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