Triethylamine → 4-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 604265Notes

Reaction equation

F[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]2[C:3]=1[CH2:4][N:5]([CH3:15])[C:6]2=[O:14].C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>CS(C)=O.O>[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([C:2]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]3[C:3]=2[CH2:4][N:5]([CH3:15])[C:6]3=[O:14])[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:30])[CH3:31]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 4-fluoro-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one (2.0 g, 8.52 mmol) and potassium carbonate (657.9 mg, 4.76 mmol), triethylamine (2.0 mL, 14.3 mmol) in dimethylsulfoxide (20 mL), piperazine-1-carboxylic acid tert-butyl ester (1.77 g, 9.52 mmol) is added and the mixture is stirred at 60° C. for 6 hours. The mixture is poured into iced water and the resulting brown solids are collected by filtration. The obtained solid is dried in vacuo at 50° C. to afford 4-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester as brown solid in 75% yield. Rf=0.25 (Hexane/AcOEt=1/1). 1H-NMR (400 MHz, CDCl3, δ, ppm): 1.50 (s, 9H), 3.13 (t, 4H), 3.20 (s, 3H), 3.61 (t, 4H), 4.37 (s, 2H), 7.04 (d, 1H), 7.78 (d, 1H).

Workup

additionis added
filtrationthe resulting brown solids are collected by filtration
customThe obtained solid is dried in vacuo at 50° C.

Sources & evidence

ORD record: ord-3c2194f0aba54b4f9b0f6e2d06b5f001
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910585B2

Reaction notes

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