Water → 1-(diphenylmethyl)-N-methyl-3-azetidinemethanamine

HRID 978571Notes

Reaction equation

HRID 978571 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:14]2[CH2:17][CH:16]([C:18]([NH:20][CH3:21])=O)[CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>O1CCCC1>[C:7]1([CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:14]2[CH2:17][CH:16]([CH2:18][NH:20][CH3:21])[CH2:15]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962Water3×HCID 14798Sodium HydroxideHCID 137728491-Benzhydryl-N-methylazetidine-3-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 142808971-(diphenylmethyl)-N-methyl-3-azetidinemethanamineYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3.2 g (85 mmole) of lithium aluminum hydride in 50 ml of dry tetrahydrofuran was added dropwise, a solution of 8.5 g (28 mmole) of 1-diphenylmethyl-N-methyl-3-azetidinecarboxamide in 50 ml of dry tetrahydrofuran. After the addition was complete, the reaction was refluxed for two hours, cooled to room temperature, and decomposed by the successive addition of 3.4 ml of water, 3.4 ml of 15% aqueous sodium hydroxide and 10.2 ml of water, titrating the final water addition to give a granular precipitate. The inorganic precipitate was removed by filtration, washed with tetrahydrofuran, and evaporated in vacuo. The residue was dissolved in chloroform, dried over magnesium sulfate, filtered, and evaporated in vacuo to give 7.0 g of 1-(diphenylmethyl)-N-methyl-3-azetidinemethanamine as a heavy syrup. This was used without further purification.

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. temperaturethe reaction was refluxed for two hours
  4. customto give a granular precipitate
  5. customThe inorganic precipitate was removed by filtration
  6. washwashed with tetrahydrofuran
  7. customevaporated in vacuo
  8. dissolutionThe residue was dissolved in chloroform
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-f7ce6f345eea4151af401ad1d5a9fa55
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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