Acetonitrile → 4-[2-(3-Nitro-1H-pyrazol-1-yl)ethyl]morpholine

HRID 1262295Notes

Reaction equation

HRID 1262295 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].Cl.Cl[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178526745HCID 178526745, compound

Product 1

HCID 574160964-[2-(3-Nitro-1H-pyrazol-1-yl)ethyl]morpholine

Procedure

Into an 8-dram vial, 3-Nitro-1H-pyrazole (0.50 g, 4.4 mmol), 4-(2-chloroethyl)-morpholine hydrochloride (1.23 g, 6.63 mmol), Potassium carbonate (1.83 g, 13.3 mmol), and Acetonitrile (30 mL, 600 mmol) were added. The reaction mixture was heated. The reaction was poured over ice. The reaction was partitioned with water and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (1 to 3% methanol). The collected fractions afforded 4-[2-(3-Nitro-pyrazol-1-yl)-ethyl]-morpholine a yellow solid (0.75 g, 75%).

Workup

  1. temperatureThe reaction mixture was heated
  2. additionThe reaction was poured over ice
  3. customThe reaction was partitioned with water and DCM
  4. customThe organic was separated
  5. washwashed with Brine
  6. dry with materialdried over Na2SO4
  7. filtrationThe solid was filtered
  8. washwashed with DCM
  9. customThe solvent was removed under vacuum
  10. customThe reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (1 to 3% methanol)

Sources & evidence

ORD record
ord-d65718a197b94f28ae37f0c5f4d1a414
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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