4-Nitrobenzenesulfonyl chloride → tert-Butyl 4-(4-aminophenylsulfonyl)piperazine-1-carboxylate

HRID 269826Notes

Reaction equation

HRID 269826 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)([O-])=O.C(N(CC)CC)C>CN(C=O)C>[NH2:14][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 10617209tert-Butyl 4-(4-aminophenylsulfonyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Boc-piperazine and 4-nitrobenzenesulfonyl chloride were allowed to undergo the reaction in DMF in the presence of triethylamine, and then the nitro group was reduced in the sama manner as the catalytic hydrogenation shown in Reference Example 3 to obtain tert-butyl 4-[(4-aminophenyl)sulfonyl]piperazine-1-carboxylate. FN: 340.

Sources & evidence

ORD record
ord-45995bc4de344d358313b90180261fa9
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Reaction notes

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