HCID 24902952, compound → HCID 28904394, compound

HRID 2218742Notes

Reaction equation

HRID 2218742 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:4]([N+:17]([O-])=O)[CH:3]=1.[H][H]>C(OCC)(=O)C.[Pt]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24902952HCID 24902952, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 28904394HCID 28904394, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve (4-bromo-2-nitro-phenyl)-(2-morpholin-4-yl-ethyl)-amine (15.3 g, 46.4 mmol) in ethyl acetate (1 L) and add 5% Pt/C (sulfided) (382 mg). Place the slurry under 60 psi hydrogen gas at room temperature of 8 h. Filter and concentrate to give 23 g crude product as a dark red oil. Purify using a short plug of silica gel and 10% 2N NH3 in MeOH/dichloromethane to give 13.5 g of a brown oil. HPLC (ISO60-10M) t=1.46 (94%), MS (ES) 301 (M+1).

Workup

  1. customat room temperature
  2. customof 8 h
  3. filtrationFilter
  4. concentrationconcentrate
  5. customto give 23 g crude product as a dark red oil
  6. customPurify

Sources & evidence

ORD record
ord-74108d8fcb724ca38a9c97973e48b6fe
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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