Trifluoroacetic acid → 4-(4-Ethylpiperazin-1-yl)-2-nitroaniline

HRID 58135Notes

Reaction equation

HRID 58135 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(=O)OC(C)(C)C)=[C:11]([N+:23]([O-:25])=[O:24])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([N+:23]([O-:25])=[O:24])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118024395tert-Butyl 4-(4-ethylpiperazin-1-yl)-2-nitrophenylcarbamate

Product 1

HCID 1180248134-(4-Ethylpiperazin-1-yl)-2-nitroanilineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-ethylpiperazin-1-yl)-2-nitrophenylcarbamate (3.3 g, 9.43 mmol) in DCM (50 mL) was added TFA (20 mL) at 0° C., the resulting mixture was stirred for 3 hours at rt. After removal of all volatiles in vacuo, the residue was re-dissolved in DCM, neutralized with saturated aqueous K2CO3 and extracted with DCM. The combined extracts were concentrated to obtain the title compound (2.1 g, yield: 90%), which was used directly in the next step. 1H NMR (400 MHz, DMSO-d6) δ 1.02 (t, 3H), 2.36 (q, 2H), 2.47-2.49 (m, 4H) 2.97-3.00 (m, 4H), 6.97 (d, 1H), 7.20 (s, 2H), 7.25 (s, 1H), 7.34 (dd, 1H); MS (ESI): 251 [M+H]+.

Workup

  1. customAfter removal of all volatiles in vacuo
  2. dissolutionthe residue was re-dissolved in DCM
  3. extractionextracted with DCM
  4. concentrationThe combined extracts were concentrated

Sources & evidence

ORD record
ord-2f97e959107a49d2b282ab412b500439
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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