Triethylamine → Tert-butyl 4-(4-cyano-3-nitrophenyl)piperazine-1-carboxylate

HRID 1520111

Reaktionsgleichung

Reaktionsgleichung von HRID 1520111
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.Cl.[C:14]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CCN(CC)CC>CN(C=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:24]2[CH2:23][CH2:22][N:21]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:26][CH2:25]2)=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11])#[N:7]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2925354-Bromo-2-nitrobenzonitrileHCID 2755973Tert-butyl Piperazine-1-carboxylate Hydrochloride

Produkt 1

HCID 51354044Tert-butyl 4-(4-cyano-3-nitrophenyl)piperazine-1-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of a mixture of compound 17 (3 g, 13.27 mmol) and 1-boc-piperazine hydrochloride (3.53 g, 15.92 mmol) in DMF (30 mL) was added Et3N (4.4 mL, 31.8 mmol), and the mixture was heated at 70° C. for 6 h. The mixture was cooled to room temperature, extracted with ethyl acetate (100 mL), and the organic layer was washed with brine (20 mL), dried over Na2SO4 and evaporated. Trituration with diethyl ether afforded 4.27 g (97%) of compound 18 as bright yellow solid, m.p. 138-139° C.; IR (KBr) νmax. cm−1: 3042 (Ar—H), 2252 (CN), 1690 (C═O), 1610, 1520, 1412 (C═C). 1H NMR (500 MHz, DMSO-d6) δ=1.39 (s, 9H, (CH3)3C); 3.44 (br. s, 4H, 2 CH2); 7.19 (dd, 1H, J=2.6, 9.4 Hz, H-5); 7.46 (d, 1H, J=2.7 Hz, H-2); 8.17 (d, 1H, J=2.7 Hz, H-6); 13C NMR (125.7 MHz, DMSO-d6) δ=28.11 (CH3)3C), 45.92 (CH2), 46.02 (CH2), 79.56 (CH3)3C), 109.24 (C-4), 115.61 (C-2), 116.46 (CN), 119.03 (C-6), 128.09 (C-5), 135.85 (C-3), 153.30 (C-1), 154.13 (C═O). Calculated (%) for C16H20N4O4 (332.15); C: 57.82, H: 6.07, N: 16.86. found (%); C: 57.76, H: 6.11, N: 16.80.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (100 mL)
  3. washthe organic layer was washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-051b4d12ba794faba152cae954dbc016
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073900B2

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