tert-Butyl piperazine-1-carboxylate → 4-(4-Cyclopropanesulfonyl-2,3-difluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1820811Notes

Reaction equation

[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10](F)=[C:9]([F:14])[C:8]=2[F:15])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C)C(=O)C>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:10]2[CH:11]=[CH:12][C:7]([S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])=[C:8]([F:15])[C:9]=2[F:14])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 90 °C

Procedure

To 4.2 mmol 1-cyclopropanesulfonyl-2,3,4-trifluoro-benzene in 20 ml N,N-dimethylacetamide was added 8.9 mmol tert-butyl-1-piperazine carboxylate, and the mixture was heated at 90° C. for 1 h. The mixture was then cooled to room temperature and concentrated in vacuo. The residue was chromatographed on silica gel (eluant: dichloromethane/ethyl acetate gradient) to afford the title compound. MS (m/e): 403.3 (M+H+, 100%)

Workup

temperatureThe mixture was then cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel (eluant: dichloromethane/ethyl acetate gradient)

Sources & evidence

ORD record: ord-c87ce15f05ee4fbe95c086a053358e59
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605163B2

Reaction notes

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