Methyl iodide → 1-Benzhydryl-2-(alpha-methylaminobenzyl)azetidine

HRID 1390963Notes

Reaction equation

HRID 1390963 reaction equation
[CH:1]([N:14]1[CH2:17][CH2:16][CH:15]1[CH:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>CN(C)C=O>[CH:1]([N:14]1[CH2:17][CH2:16][CH:15]1[CH:18]([NH:25][CH3:28])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 203452731-Benzhydryl-2-(alpha-aminobenzyl)azetidine

Product 1

HCID 203452871-Benzhydryl-2-(alpha-methylaminobenzyl)azetidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-25 °C

Procedure

To a stirred solution of 2.50 g of 1-benzhydryl-2-(α-aminobenzyl)azetidine in 25 ml. of N,N-dimethylformamide, add 365 mg. of a 55% dispension of sodium hydride. Stir the mixture under a nitrogen atmosphere and when frothing subsides, warm and maintain the stirred mixtuure at 40° for twenty mintues. Cool the mixture to -25° C. and add 1.20 g. of methyl iodide. Remove the reaction mixture from the cooling bath and allow it to warm to room temperature. After ca. 15 minutes at room temperature, pour the contents of the reaction flask into a stirred mixture of 100 ml. of water and 25 ml. of ether. Separate the layers and re-extract the aqueous phase with ether. Combine all ether extracts, wash successively with water and brine, dry over anhydrous sodium sulfate, and strip off solvent in vacuo. Crystallize the residual solid from ether to obtain the analytically pure title compound containing 1/4 mole of water-of-crystallization and having m.p. 111°-113°.

Workup

  1. temperaturewhen frothing subsides, warm
  2. temperaturemaintain the stirred mixtuure at 40° for twenty mintues
  3. additionadd 1.20 g
  4. customRemove the reaction mixture from the cooling bath
  5. temperatureto warm to room temperature
  6. additionpour the contents of the reaction flask
  7. additioninto a stirred mixture of 100 ml
  8. customSeparate the layers
  9. extractionre-extract the aqueous phase with ether
  10. washwash successively with water and brine
  11. dry with materialdry over anhydrous sodium sulfate, and strip off solvent in vacuo
  12. customCrystallize the residual solid from ether

Sources & evidence

ORD record
ord-4c2faa375f12426ba9bb99e6b0da4362
Source dataset
uspto-grants-1979_02
Patent number
US04140780

Reaction notes

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