Stannous chloride dihydrate → HCID 25014604, compound

HRID 1876821Notes

Reaction equation

HRID 1876821 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH2:21][CH2:20]2)=[O:18])=[C:11]([N+:31]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl>CO>[NH2:31][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([O:15][CH3:16])=[CH:13][C:12]=1[C:17]([N:19]1[CH2:20][CH2:21][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH2:23][CH2:24]1)=[O:18]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 66882276HCID 66882276, compound

Product 1

HCID 25014604HCID 25014604, compoundYield 139.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(2-pyridyl)piperazino]methanone (7b) (500 mg, 1.11 mmol) was dissolved in methanol (10 mL), SnCl2.2H2O (753 mg, 3.3 mmol) was added and refluxed until the TLC indicated the completion of the reaction. The methanol was evaporated by vacuum and the aqueous layer was then adjusted to pH 8 with 10% NaHCO3 solution and extracted with ethyl acetate (2×30 mL). The combined organic phase was dried over Na2SO4 and evaporated under vacuum to afford the crude (450 mg, 95% yield), This was further purified by column chromatography using ethyl acetate:hexane (6:4) as a solvent system to obtain the pure product 8b (650 mg, in 94% yield). 1H NMR (CDCl3) δ 3.15-3.30 (m, 4H), 3.70-3.80 (m, 4H), 3.95 (s, 3H), 5.20 (s, 2H), 6.20 (s, br,) 7.00-7.50 (m, 5H), 7.70 (s, 1H), 8.25-8.35 (d, J=9.05, 2H); FABMS: 418 (M+H)+.

Workup

  1. temperaturerefluxed until the TLC
  2. customthe completion of the reaction
  3. customThe methanol was evaporated by vacuum
  4. extractionextracted with ethyl acetate (2×30 mL)
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. customevaporated under vacuum
  7. customto afford the crude (450 mg, 95% yield)
  8. customThis was further purified by column chromatography

Sources & evidence

ORD record
ord-781e23e2d1f04c38a9d3144adc407d58
Source dataset
uspto-grants-2012_11
Patent number
US08309726B2

Reaction notes

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