HCID 68817628, compound → HCID 68818352, compound

HRID 735106Notes

Reaction equation

HRID 735106 reaction equation
[Br:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[H][H]>[Ni].C(OCC)(=O)C>[Br:1][C:2]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 68817628HCID 68817628, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68818352HCID 68818352, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture of 220 mg (0.66 mmol) of 4-[2-(2-bromo-4-nitrophenoxy)ethyl]morpholine and 100 mg Raney nickel in 50 mL of ethyl acetate is hydrogenated at ambient temperature and 3 bar hydrogen. The catalyst is suction filtered and the filtrate is evaporated down. The purification is carried out by column chromatography on aluminum oxide (eluant: petroleum ether/ethyl acetate (1:1)). Yield: 100 mg (50% of theory); C12H17BrN2O2 (M=301.18); calc.: molecular ion peak (M+H)+: 301/303 (Br); found: molecular ion peak (M+H)+: 301/303 (Br).

Workup

  1. customis hydrogenated at ambient temperature
  2. filtrationfiltered
  3. customthe filtrate is evaporated down
  4. customThe purification

Sources & evidence

ORD record
ord-8eaf70bc4790422e9db948424c98175b
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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