Methanesulfonyl chloride → Tert-Butyl 4-(2-[(Methylsulfonyl)Amino]Phenyl)-Piperazinecarboxylate

HRID 228072Notes

Reaction equation

HRID 228072 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].CCN(C(C)C)C(C)C>N1C=CC=CC=1>[CH3:21][S:22]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 2795530tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylate

Product 1

HCID 21935212Tert-Butyl 4-(2-[(Methylsulfonyl)Amino]Phenyl)-PiperazinecarboxylateYield 72.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl 4-{(2-[(methylsulfonyl)amino]phenyl}-piperazinecarboxylate was prepared following the procedure for Preparation III using, tert-butyl 4-(2-aminophenyl)piperazinecarboxylate (4.4 g, 16 mmol), methanesulfonyl chloride (1.4 mL, 18 mmol) and DIEA (instead of pyridine) (3.1 mL, 18 mmol). The crude material was purified by flash chromatography (SiO2, 4:1 hexane:EtOAc) and concentrated in vacuo to afford the desired compound (4.1 g). MS (ESI, pos. ion) m/z: 356 (M+H), (ESI, neg. ion) m/z: 354 (M−H). Calc'd for C16H25N3O4S: 355.16.

Workup

  1. customtert-Butyl 4-{(2-[(methylsulfonyl)amino]phenyl}-piperazinecarboxylate was prepared
  2. customThe crude material was purified by flash chromatography (SiO2, 4:1 hexane:EtOAc)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d76fbf0521e4f2792f8f8bfb8850ed8
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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