HCID 783358, compound → HCID 67234975, compound

HRID 1521738Notes

Reaction equation

HRID 1521738 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([CH:14]=1)[CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>CC(O)=O.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:15])=[C:6]([CH2:7][N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:14]=1

Participants

4

Reactant 1

HCID 783358HCID 783358, compound

Product 1

HCID 67234975HCID 67234975, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(5-chloro-2-nitrobenzyl)morpholine (5.1 g, 19.9 mmol) in HOAc (75 mL) is carefully added zinc dust (3.9 g, 59.6 mmol). After 2 hours, the reaction is filtered through a bed of Celite and the filtrate is concentrated to remove most of the HOAc. The residue is then taken up in 2M aqueous K2CO3 and extracted with ethyl acetate. The organic layer is dried (Na2SO4) and concentrated to afford a brown oil. The crude material is purified by flash column chromatography using a gradient of 0-5% methanol/CH2Cl2 to afford the title compound (4.0 g, 12.4 mmol, 70% purity).

Workup

  1. filtrationthe reaction is filtered through a bed of Celite
  2. concentrationthe filtrate is concentrated
  3. customto remove most of the HOAc
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. concentrationconcentrated
  7. customto afford a brown oil
  8. customThe crude material is purified by flash column chromatography

Sources & evidence

ORD record
ord-c02d1c26c2394570a584737d8b4c1a15
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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