Stannous Chloride → HCID 63166005, compound

HRID 491691Notes

Reaction equation

HRID 491691 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][CH:7]([N:10]([CH3:12])[CH3:11])[CH2:6]1.Cl[Sn]Cl>CCO>[NH2:17][C:14]1[CH:15]=[CH:16][C:2]([Cl:1])=[C:3]([CH:13]=1)[CH2:4][N:5]1[CH2:9][CH2:8][CH:7]([N:10]([CH3:11])[CH3:12])[CH2:6]1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 55160281HCID 55160281, compound

Product 1

HCID 63166005HCID 63166005, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

[1-(2-Chloro-5-nitro-benzyl)-pyrrolidin-3-yl]-dimethyl-amine (Step e, 7 g, 24.7 mmol, 1.0 eq.) was dissolved into EtOH (400 ml). SnCl2 (14 g, 74.1 mmol, 3.0 eq.) was added and the reaction was heated to 80° C. for 18 h. The mixture was cooled down to RT and quenched with 1N K2CO3 (aq.) until bubbling had ceased. The white solids that had formed were filtered over Celite® and washed with EtOH. The filtrate was concentrated and redissolved in EtOAc (100 mL). Washed with 2 N NaOH (50 ml) and 2N NaOH/brine (50 mL). The organic layer was dried (MgSO4), filtered and concentrated to yield [1-(5-amino-2-chloro-benzyl)-pyrrolidin-3-yl]-dimethyl-amine.

Workup

  1. temperatureThe mixture was cooled down to RT
  2. customquenched with 1N K2CO3 (aq.)
  3. customuntil bubbling
  4. customThe white solids that had formed
  5. filtrationwere filtered over Celite®
  6. washwashed with EtOH
  7. concentrationThe filtrate was concentrated
  8. dissolutionredissolved in EtOAc (100 mL)
  9. washWashed with 2 N NaOH (50 ml) and 2N NaOH/brine (50 mL)
  10. dry with materialThe organic layer was dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-c3955c0820284e8b93238f275ce434f4
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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