Stannous Chloride → 2-(4-Benzylpiperazin-1-yl)aniline

HRID 1419582Notes

Reaction equation

[Sn](Cl)Cl.[CH2:4]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-])=O)[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:14]1[CH2:13][CH2:12][N:11]([CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 70 °C

Procedure

Tin (II) chloride (12.77 g, 67 mmol) was added to a solution of 1-benzyl-4-(2-nitrophenyl)piperazine (4.0 g, 13 mmol) in ethanol (50 mL) and the mixture was heated at 70° C. for 1 h. The solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate and washed with aqueous sodium hydroxide (2M, 4×). The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/Hexane (80:20 increasing to 75:25) to give the title compound as a pale yellow solid (2.61 g, 72%), δH (250 MHz, CDCl3) 7.38-7.25 (5H, m), 7.03-6.89 (2H, m), 6.77-6.70 (2H, m), 4.05-3.90 (2H, br s), 3.59 (2H, s), 2.96-2.92 (4H, m), and 2.65-2.55 (4H, br s).

Workup

customThe solvent was evaporated under reduced pressure
additionthe residue was diluted with ethyl acetate
washwashed with aqueous sodium hydroxide (2M, 4×)
dry with materialThe organic layer was dried (MgSO4)
customthe solvent was evaporated under reduced pressure
customThe residue was purified by flash column chromatography on silica gel
washeluting with EtOAc/Hexane (80:20 increasing to 75:25)

Sources & evidence

ORD record: ord-d14e0ecd57734c38bf42c673fffed5df
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05885999

Reaction notes

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