1-(2,5-Xylyl)piperazine → HCID 67141139, compound

HRID 1864365Notes

Reaction equation

[C:1]1([S:7]([NH:10][CH:11]([CH2:15][OH:16])[C:12]([OH:14])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.OS([O-])(=O)=O.[K+]>O1CCCC1.C(OCC)(=O)C>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[N:25]1[CH2:26][CH2:27][N:28]([C:12](=[O:14])[CH:11]([NH:10][S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])[CH2:15][OH:16])[CH2:29][CH2:30]1

Participants

Conditions

Temperature: 0 °C

Procedure

(RS)-2-benzenesulfonylamino-3-hydroxy-propionic acid (1.204 g) was dissolved in tetrahydrofuran (15 ml) and cooled to 0° C. 1-(2,5-Dimethylphenyl)-piperazine (1.12 g), (benzotriazol-1-yloxy)-tris-(dimethylamino)-phosphonium-hexafluorophosphate (BOP reagent, 3.26 g) and N-ethyl-diisopropylamine (1.90 g) were added. The mixture was stirred at room temperature for 18 h. Ethyl acetate and a 10% KHSO4 solution were added. The organic phase was washed with water, dried, filtered and evaporated. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:1=>ethyl acetate) to give (RS)—N-{2-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-1-hydroxymethyl-2-oxo-ethyl}-benzenesulfonamide (1.45 g) as a colorless foam. MS: 418.3 ([M+H]+)

Workup

washThe organic phase was washed with water
customdried
filtrationfiltered
customevaporated
customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:1=>ethyl acetate)

Sources & evidence

ORD record: ord-995bdd049fec4548b55de229e263bed1
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625902B2

Reaction notes

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