HCID 57812840, compound → HCID 57812830, compound

HRID 2274433Notes

Reaction equation

HRID 2274433 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([NH2:20])[C:17]([N+:21]([O-])=O)=[CH:16][C:15]=2[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[CH:16][C:15]=2[F:24])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 57812840HCID 57812840, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57812830HCID 57812830, compoundYield 109.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.4 g of 4-(5-amino-2-fluoro-4-nitrophenyl)piperazine-1-carboxylic acid tert-butyl ester in solution in 20 mL of methanol are hydrogenated under 1 bar of hydrogen pressure in the presence of 139 mg of palladium-on-charcoal at 22° C. for 16 hours. The reaction crude is filtered through celite and the filtrate is concentrated under vacuum in a rotary evaporator. 1.4 g of 4-(4,5-diamino-2-fluorophenyl)piperazine-1-carboxylic acid tert-butyl ester are isolated in the form of a brown resin. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.41 (s, 9H); 2.73 (m, 4H); 3.40 (m, 4H); 4.23 (broad s, 2H); 4.37 (broad s, 2H); 6.27 (d, J=8.5 Hz, 1H); 6.31 (d, J=13.5 Hz, 1H). EI mass spectrum: m/z=310 M+. (base peak), m/z=254 (M-C4H)+, m/z=57 C4H+.

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-1ef1a8e7be0a401295cb6811b35eb2cd
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

Loading…