Tin dichloride dihydrate → HCID 68634976, compound

HRID 2244044Notes

Reaction equation

HRID 2244044 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=2[N+:24]([O-])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl.O>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=2[NH2:24])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 68634606HCID 68634606, compound

Product 1

HCID 68634976HCID 68634976, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(5-Methyl-2-nitro-phenyl)-piperazine-1-carboxylic acid benzyl ester (5.60 g; 15.7 mmol) and SnCl2.H2O (17.5 g; 77.6 mmol) were refluxed in 100 mL ethanol for 2½ hours. Ethanol was removed in vacuo. The residue was poured into 300 mL saturated NaHCO3. The mixture was extracted with ethyl acetate (2×250 mL). The organic phase was washed with brine (2×100 mL), dried with MgSO4, filtered through a pad of silica and concentrated in vacuo to give 4.71 g (14.5 mmol; 91.6%) 4-(2-amino-5-methyl-phenyl)-piperazine-1-carboxylic acid benzyl ester.

Workup

  1. customEthanol was removed in vacuo
  2. additionThe residue was poured into 300 mL saturated NaHCO3
  3. extractionThe mixture was extracted with ethyl acetate (2×250 mL)
  4. washThe organic phase was washed with brine (2×100 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered through a pad of silica
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ba45557a8a04282a9d02185ce8889f7
Source dataset
uspto-grants-2010_03
Patent number
US07678800B2

Reaction notes

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