Hydrochloric Acid → N-(1-(3-Bromophenyl)ethyl)-2-nitro-5-(piperazin-1-yl)benzenamine hydrochloride

HRID 2426002Notes

Reaction equation

HRID 2426002 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:11]2[CH:12]=[C:13]([N:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[ClH:33].CCOCC>ClCCl>[ClH:33].[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:11]2[CH:12]=[C:13]([N:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 58707273t-Butyl 4-(3-(1-(3-bromophenyl)ethylamino)-4-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 67147328N-(1-(3-Bromophenyl)ethyl)-2-nitro-5-(piperazin-1-yl)benzenamine hydrochlorideYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-(3-(1-(3-bromophenyl)ethylamino)-4-nitrophenyl)piperazine-1-carboxylate (0.45 g, 0.9 mmol), 2N HCl in ether (10 mL, 20.0 mmol) and dichloromethane (5 mL) was stirred for 18 h and concentrated in vacuo. The residue was dissolved in dichloromethane; this solution was washed with aqueous NaHCO3 solution, dried over Na2SO4 and concentrated in vacuo. The yellow solid residue was dissolved in dichloromethane (0.5 mL) and reacted with 1N HCl in ether (1 mL). The resulting precipitates were collected by vacuum filtration, washed with ether and air dried to yield the title compounds as a yellow solid (0.13 g, 33%). 1H NMR (400 MHz, CDCl3): δ 8.71 (d, 1H), 8.05 (d, 1H), 7.50 (s, 1H), 7.39 (m, 1H), 7.23 (m, 2H), 6.19 (dd, 1H), 5.60 (d, 1H), 4.53 (m, 1H), 3.21 (m, 2H), 3.13 (m, 2H), 2.88 (m, 4H), 1.63 (d, 3H). MS (ESI) m/z: Calculated: 404; Observed: 405 (M+H+).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthis solution was washed with aqueous NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe yellow solid residue was dissolved in dichloromethane (0.5 mL)
  7. customreacted with 1N HCl in ether (1 mL)
  8. customThe resulting precipitates
  9. filtrationwere collected by vacuum filtration
  10. washwashed with ether and air
  11. customdried

Sources & evidence

ORD record
ord-e099a327fb21424b8c4b3141b0d40a1f
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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