Water → 3-Aminomethyl-1-benzhydrylazetidine

HRID 1796970Notes

Reaction equation

HRID 1796970 reaction equation
[C:1]1([CH:7]([N:14]2[CH2:17][CH:16]([C:18]#[N:19])[CH2:15]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[Na]>O1CCCC1>[NH2:19][CH2:18][CH:16]1[CH2:15][N:14]([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:17]1

Participants

6

Reactant 4

HCID 962Water2×HCID 27792901-(Diphenylmethyl)azetidine-3-carbonitrileHCID 5360545SodiumHCID 21226445Aluminium lithium hydride

Product 1

HCID 100378743-Aminomethyl-1-benzhydrylazetidineYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(1,1-diphenylmethyl)azetidine-3-carbonitrile (7.8 g, 31.4 mmol) in 30 mL of tetrahydrofuran was slowly added to a suspension of lithium aluminium hydride (4.0 g, 105 mmol) in tetrahydrofuran under nitrogen and the resulting mixture was stirred under reflux for one hour. On cooling, the mixture was treated dropwise with water (4 mL), aqueous sodium hydroxyde (4 mL, 4N), and water (12 mL) and filtered. The filtrate was concentrated under reduced pressure to yield 3-(aminomethyl)-1-(1,1-diphenylmethyl)azetidine as a white solid (5.2 g, 73%).

Workup

  1. temperatureunder reflux for one hour
  2. temperatureOn cooling
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc55b5e77a9341ebaa8122f04acaf301
Source dataset
uspto-grants-2006_04
Patent number
US07034016B2

Reaction notes

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