1,2-Difluoro-4-nitrobenzene → 1-(2-Fluoro-4-nitrophenyl)-4-(4-methoxyphenyl)piperazine

HRID 527196Notes

Reaction equation

HRID 527196 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1>C(#N)C>[F:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:23]1[CH2:22][CH2:21][N:20]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 1230531,2-Difluoro-4-nitrobenzeneHCID 2697221-(4-Methoxyphenyl)piperazine

Product 1

HCID 712952521-(2-Fluoro-4-nitrophenyl)-4-(4-methoxyphenyl)piperazineYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension containing 0.16 g of 1,2-difluoro-4-nitrobenzene (2) and 0.28 mL of N-diisopropyl ethylamine (DIPEA) in 4 mL acetonitrile, 0.19 of 1-(4-methoxyphenyl)piperazine (1) was added. The reaction mixture was stirred at room temperature for over night (12 h). The reaction mixture was filtered to get the yellowish solid. Then the collected solid was washed with hexane to get nitro compound 3 (0.25 g, 75%). 1H NMR (400 MHz, CDCl3, δH): 8.01 (dd, J=8.8, 2.4 Hz, 1H), 7.93 (dd, J=12.8, 2.4 Hz, 1H), 6.99-6.97 (m, 3H), 6.89-6.87 (m, 2H), 3.79 (s, 3H), 3.47 (bs, 4H), 3.26 (d, J=4.8 Hz, 4H). 13C NMR (100 MHz, CDCl3, δC): 154.4, 151.9, 121.0, 118.9, 117.3, 114.6, 112.8, 112.5, 55.6, 51.0, 49.6.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. customto get the yellowish solid
  4. washThen the collected solid was washed with hexane

Sources & evidence

ORD record
ord-23137fead7c742ad833adfe4b52d9374
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

Loading…