Stannous chloride dihydrate → 1-(4-Hydrazinobenzyl)-4-methylpiperazine

HRID 501221

Reaktionsgleichung

Reaktionsgleichung von HRID 501221
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[N:16]([O-])=O.[Na+].O.O.Cl[Sn]Cl>C(O)(=O)C.O.Cl>[NH:13]([C:12]1[CH:14]=[CH:15][C:9]([CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:10][CH:11]=1)[NH2:16]

Komponenten

7

Edukt 3

HCID 61436Stannous chloride dihydrateHCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 684652221-(4-Hydrazinobenzyl)-4-methylpiperazineAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-[(4-methylpiperazin-1-yl)methyl]aniline (3.2 g, 15.57 mmol) in acetic acid: concentrated HCl (32:32 mL) at 10° C. was added NaNO2 (1.30 g, 18.78 mmol) in water (16 mL) and stirred for 10 min. Freshly prepared SnCl2.2H2O (11.75 g, 51.97 mmol) in concentrated HCl (32 mL) was added at 10° C. The temperature of the reaction mixture was allowed to rise to room temperature and maintained there for 4 hr. After filtering the reaction mixture, the precipitate was washed with water and the solid obtained was dried under reduced pressure to obtain 1-(4-hydrazinobenzyl)-4-methylpiperazine (3.4 g). 1H NMR (CD3OD, 200 MHz) δ: 7.66 (2H, d, J=8.4 Hz), 7.13 (2H, d, J=8.4 Hz), 4.46 (2H, s), 3.72 (8H, bm), 3.11 (3H, s);

Aufarbeitung

  1. customto rise to room temperature
  2. temperaturemaintained there for 4 hr
  3. filtrationAfter filtering the reaction mixture
  4. washthe precipitate was washed with water
  5. customthe solid obtained
  6. customwas dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-09f2e740fd884df3b87df1985fce89cf
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772245B2

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