HCID 57812838, compound → HCID 57812833, compound

HRID 2274424Notes

Reaction equation

HRID 2274424 reaction equation
[F:1][C:2]1[C:7]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([CH3:15])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH2:16])=[C:4]([N+:17]([O-])=O)[CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]([NH2:16])=[CH:6][C:7]=1[N:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH3:15])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 57812838HCID 57812838, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57812833HCID 57812833, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

20.9 g of 4-fluoro-5-(4-methylperhydro-1,4-diazepin-1-yl)-2-nitrophenylamine in solution in 750 mL of methanol are hydrogenated under 1 bar of hydrogen pressure in the presence of 2 g of palladium-on-charcoal at 25° C. for 16 hours. The reaction crude is filtered through celite and the filtrate is concentrated under vacuum in a rotary evaporator. 19.1 g of 4-fluoro-5-(4-methylperhydro-1,4-diazepin-1-yl)benzene-1,2-diamine in the form of a black oil are isolated. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.82 (m, 2H); 2.26 (s, 3H); 2.56 (m, 4H); 3.11 (m, 4H); 4.19 (broad m, 4H); from 6.22 to 6.31 (m, 2H). EI m/z=238: M+. (base peak)—m/z=223: (M-CH3)+—m/z=168: (M−C4H8N)+—m/z=70: C4H8N+—m/z=57: C3H7N+.

Workup

  1. customThe reaction crude
  2. filtrationis filtered through celite
  3. concentrationthe filtrate is concentrated under vacuum in a rotary evaporator

Sources & evidence

ORD record
ord-8cb14cf7b42e4b0fbca00bfc45640daa
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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