Sodium triacetoxyborohydride → 2-Fluoro-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

HRID 1519600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519600
[F:1][C:2]1[CH:9]=[C:8]([CH2:10][CH:11]=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:18][CH:17]=1)([O-:15])=[O:14].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([CH2:10][CH2:11][N:27]2[CH2:28][CH2:29][N:24]([CH2:23][CH2:22][C:19]3[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=3)[CH2:25][CH2:26]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 149859651-[2-(4-Nitrophenyl)ethyl]piperazineHCID 866944782-Fluoro-4-(2-oxoethyl)benzonitrile

Produkt 1

HCID 680713482-Fluoro-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2-fluoro-4-(2-oxoethyl)benzonitrile (140 mg, 0.88 mmol), 1-[2-(4-nitrophenyl)ethyl]piperazine (170 mg, 0.73 mmol) and NaBH(OAc)3 (620 mg, 2.9 mmol) in anhydrous DCM (10 mL) was stirred at ambient temperature overnight. The reaction was completed according to TLC. The reaction mixture was added 20 mL of DCM, washed with brine, separated the organic layer, dried over anhydrous sodium sulfate and concentrated. The residue was purified by preparative TLC to give the product. 1H-NMR (400 MHz, CDCl3) δ ppm 8.13˜8.16 (d, J=8.6 Hz, 2H), 7.52˜7.55 (t, J=6.6 Hz, 1H), 7.36˜7.38 (d, J=8.6 Hz, 2H), 7.08˜7.12 (m, 2H), 2.89˜3.00 (m, 4H), 2.56˜2.78 (m, 12H). MS m/z: 383 (M+1)+. (0.24 μM)

Aufarbeitung

  1. washwashed with brine
  2. customseparated the organic layer
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC
  6. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-4dd76851c35043ec9b9b92ac4b15d79e
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073882B2

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