1-Methylpiperazine → 1-[(5-Bromo-2,3-dihydro-1-benzofuran-2-yl)carbonyl]-4-methylpiperazine

HRID 1778660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778660
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([C:10]([OH:12])=O)[CH2:7][C:6]=2[CH:13]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:41][N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1.C(N(CC)C(C)C)(C)C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([C:10]([N:45]3[CH2:46][CH2:47][N:42]([CH3:41])[CH2:43][CH2:44]3)=[O:12])[CH2:7][C:6]=2[CH:13]=1

Komponenten

5

Edukt 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 186242435-Bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid

Produkt 1

HCID 867228101-[(5-Bromo-2,3-dihydro-1-benzofuran-2-yl)carbonyl]-4-methylpiperazineAusbeute 99,9 %

Versuchsvorschrift

A mixture of 5-bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid (0.243 g, 1.00 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.464 g, 1.05 mmol), 1-methyl-piperazine (116 μL, 1.05 mmol) and N,N-diisopropylethylamine (696 μL, 4.00 mmol) was stirred at r.t. for 2 h. The volatiles were removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (gradient: 0-50%) to afford the desired product (0.325 g, 95%). LCMS (M+H)+=324.9/327.0.

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (gradient: 0-50%)

Quellen und Nachweise

ORD-Eintrag
ord-7f5c0867b051404a97e33382276cfff8
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266892B2

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