Benzene, 1-fluoro-2-methyl-4-nitro- → tert-Butyl 4-(2-methyl-4-nitrophenyl)piperazine-1-carboxylate

HRID 545233Notes

Reaction equation

HRID 545233 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[CH3:24].C(N(CC)C(C)C)(C)C>CS(C)=O>[CH3:24][C:16]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:15]=1[N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22336105tert-Butyl 4-(2-methyl-4-nitrophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as in Production Example 5-1, but using tert-butyl piperazine-1-carboxylate in place of N-ethylpiperazine used in Production Example 5-1, using 2-fluoro-5-nitrotoluene in place of 2-fluoro-5-nitrobenzyl alcohol, using N,N-diisopropylethylamine in place of potassium carbonate, and using dimethylsulfoxide in place of N-methylpyrrolidone, 4.91 g of crude tert-butyl 4-[2-methyl-4-nitrophenyl]piperazine-1-carboxylate was obtained as a yellow solid.

Sources & evidence

ORD record
ord-868f69b5c7c24614aa5df62cdb79badf
Source dataset
uspto-grants-2011_05
Patent number
US07935708B2

Reaction notes

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