Stannous chloride dihydrate → 3-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-4-iodobenzamide

HRID 2281183Notes

Reaction equation

HRID 2281183 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([I:17])=[C:13]([N+:18]([O-])=O)[CH:12]=1)[CH2:2]2.O.O.[Sn](Cl)Cl>CN(C=O)C>[NH2:18][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[I:17])[C:10]([NH:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)=[O:21]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 58932946N-(1-Azabicyclo[2.2.2]oct-3-yl)-4-iodo-3-nitrobenzamide

Product 1

HCID 589329423-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-4-iodobenzamideYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 100 mg (0.25 mmol) of N-(1-azabicyclo[2.2.2]oct-3-yl)-4-iodo-3-nitrobenzamide and 281 mg (1.25 mmol) of tin(II) chloride dihydrate in 5 ml of DMF was stirred at room temperature for 6 h. The solvent was distilled off in a rotary evaporator, the residue was taken up in 10 ml of dichloromethane, and 10 ml of aqueous 1 M sodium hydroxide solution were added. The organic phase was dried over sodium sulfate, and the solvent was distilled off in a rotary evaporator. 91 mg (98%) of the desired title compound were obtained.

Workup

  1. distillationThe solvent was distilled off in a rotary evaporator
  2. addition10 ml of aqueous 1 M sodium hydroxide solution were added
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. distillationthe solvent was distilled off in a rotary evaporator

Sources & evidence

ORD record
ord-65215cff99b746bda796dc0d8ec0ec32
Source dataset
uspto-grants-2015_09
Patent number
US09139579B2

Reaction notes

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