HCID 57812854, compound → HCID 57812829, compound

HRID 2274409Notes

Reaction equation

HRID 2274409 reaction equation
[F:1][C:2]1[C:7]([N:8]2[CH2:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][C:5]([NH2:15])=[C:4]([N+:16]([O-])=O)[CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH2:15])=[CH:6][C:7]=1[N:8]1[CH2:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 57812854HCID 57812854, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57812829HCID 57812829, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7 g of 4-fluoro-2-nitro-5-perhydro-1,4-oxazepin-4-ylphenylamine in solution in 170 mL of methanol are hydrogenated under 1 bar of hydrogen pressure in the presence of 700 mg of palladium-on-charcoal at 22° C. for 10 hours. The reaction crude is filtered through celite and the filtrate is concentrated under vacuum in a rotary evaporator. After evaporation, the reaction crude is purified by flash chromatography (elution dichloromethane/methanol). 3 g of 4-fluoro-5-perhydro-1,4-oxazepin-4-ylbenzene-1,2-diamine are isolated. 1H NMR spectrum (400 MHz, DMSO-d6, δ in ppm): 1.88 (m, 2H); 3.11 (m, 4H); from 3.64 to 3.74 (m, 4H); 4.20 (broad s, 2H); 4.26 (broad s, 2H); from 6.25 to 6.31 (m, 2H).

Workup

  1. customThe reaction crude
  2. filtrationis filtered through celite
  3. concentrationthe filtrate is concentrated under vacuum in a rotary evaporator
  4. customAfter evaporation
  5. customthe reaction crude
  6. customis purified by flash chromatography (elution dichloromethane/methanol)

Sources & evidence

ORD record
ord-1d9e609a982d4a17b5eafa54726e6748
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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