Sodium Hydroxide → HCID 11086077, compound

HRID 493093Notes

Reaction equation

HRID 493093 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[I:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([NH:16][CH3:17])=O.[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C(OCC)C.C1COCC1.O>[I:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[CH2:14][NH:16][CH3:17]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 6158522-Iodo-N-methylbenzamideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 11086077HCID 11086077, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (14.8 g, 390 mmol) is suspended in dry diethyl ether (250 mL) and cooled to 0° C. Aluminum chloride (16.0 g, 121 mmol) dissolved in dry diethyl ether (250 mL) is added dropwise at 0-5° C. The cooling bath is removed and the mixture is stirred at ambient temperature for 1 hour. The resulting aluminum hydride reagent solution is cooled to 0° C. followed by dropwise addition of 2-iodo-N-methyl-benzamide (50.8 g, 195 mmol) dissolved in dry THF (500 mL). After complete addition the solution is allowed to heat to ambient temperature and stirring is continued for 16 hours. The mixture is cooled to 10° C. followed by slow dropwise addition of water (30 mL) followed by 2M sodium hydroxide (30 mL) and water (150 mL). MgSO4 is added and the mixture is stirred for 10 minutes, filtered and concentrated in vacuo. The remanence is redissolved in ethyl acetate (500 mL), dried (MgSO4) and concentrated again to furnish 45.2 g (94%) of (2-iodo-benzyl)-methyl-amine as an oil. (2-Iodo-benzyl)-methyl-amine (20.0 g, 80.9 mmol) is dissolved in dry THF (300 mL) and di-tert-butyl dicarbonate (18.5 g, 85.0 mmol) is added. The mixture is stirred for 1 hour at ambient temperature. The volatiles are removed by means of evaporation and the crude mixture is purified by silica gel chromatography eluting with ethyl acetate-heptane (1:4) to furnish 28.5 g (quant.) of the title compound as an oil.

Workup

  1. additionis added dropwise at 0-5° C
  2. customThe cooling bath is removed
  3. temperatureThe resulting aluminum hydride reagent solution is cooled to 0° C.
  4. additionAfter complete addition the solution
  5. temperatureto heat to ambient temperature
  6. stirringstirring
  7. waitis continued for 16 hours
  8. temperatureThe mixture is cooled to 10° C.
  9. stirringthe mixture is stirred for 10 minutes
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. dissolutionThe remanence is redissolved in ethyl acetate (500 mL)
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated again

Sources & evidence

ORD record
ord-5e1f26f9f66f43f6919d40aba641f493
Source dataset
uspto-grants-2009_05
Patent number
US07534791B2

Reaction notes

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