Stannous chloride dihydrate → HCID 24206030, compound

HRID 1876820Notes

Reaction equation

HRID 1876820 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][C:26]=3[O:31][CH3:32])[CH2:21][CH2:20]2)=[O:18])=[C:11]([N+:33]([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>[NH2:33][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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][C:26]=2[O:31][CH3:32])[CH2:23][CH2:24]1)=[O:18]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 66882955HCID 66882955, compound

Product 1

HCID 24206030HCID 24206030, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(2-methoxyphenyl)piperazino]methanone (7a) (500 mg, 1.04 mmol) was dissolved in methanol (10 mL), SnCl2.2H2O (706 mg, 3.14 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. This was further purified by column chromatography using ethyl acetate:hexane (6:4) as a solvent system to obtain the pure product (8a) (425 mg, 91% yield). 1H NMR (CDCl3) δ 3.20-3.30 (m, 4H), 3.45-3.55 (m, 4H), 3.85 (s, 3H), 3.98 (s, 3H), 5.20 (s, 2H), 6.19 (s, broad NH2) 6.80-7.00 (m, 5H), 7.30-7.50 (m, 5H), 7.70 (s, 1H); FABMS: 447 (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
  8. customThis was further purified by column chromatography

Sources & evidence

ORD record
ord-1ca993422ed949659306c322c86d9a6a
Source dataset
uspto-grants-2012_11
Patent number
US08309726B2

Reaction notes

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