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

HRID 501221

Reaction equation

HRID 501221 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

HCID 684652221-(4-Hydrazinobenzyl)-4-methylpiperazineYield 99.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

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);

Workup

  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

Sources & evidence

ORD record
ord-09f2e740fd884df3b87df1985fce89cf
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Linked notes

Loading…