Water → 3-Aminomethyl-1-benzhydrylazetidine

HRID 978569Notes

Reaction equation

HRID 978569 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH:9]1[CH2:12][N:11]([CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10]1)#[N:8].O.[OH-].[Na+]>O1CCCC1>[C:14]1([CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]2[CH2:12][CH:9]([CH2:7][NH2:8])[CH2:10]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962Water3×HCID 14798Sodium HydroxideHCID 27792901-(Diphenylmethyl)azetidine-3-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 100378743-Aminomethyl-1-benzhydrylazetidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5.7 g (0.15 mole) of lithium aluminum hydride in 200 ml of dry tetrahydrofuran was treated portionwise with 18.6 g (75 mmole) of solid 3-cyano-1-(diphenylmethyl)azetidine. When the addition was complete, the reaction was stirred at room temperature for two hours, refluxed for four hours, and stirred at room temperature for 18 hours. The reaction was decomposed by the successive addition of 6 ml of water, 6 ml of 15% sodium hydroxide, and 18 ml of water, titrating the final water addition to give a granular precipitate. The inorganic precipitate was removed by filtration, washed with tetra hydrofuran and evaporated in vacuo to give 16.9 g of 1-(diphenylmethyl)-3-azetidinemethanamine as a heavy oil.

Workup

  1. additionWhen the addition
  2. temperaturerefluxed for four hours
  3. stirringstirred at room temperature for 18 hours
  4. customto give a granular precipitate
  5. customThe inorganic precipitate was removed by filtration
  6. washwashed with tetra hydrofuran
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-00fede2af0964137a7e4f5edecec85ce
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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