1-Benzhydryl-2-benzimidoylazetidine → 1-Benzhydryl-2-(alpha-aminobenzyl)azetidine
Reaction equation
[CH:1]([N:14]1[CH2:17][CH2:16][CH:15]1[C:18](=[NH: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-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH:1]([N:14]1[CH2:17][CH2:16][CH:15]1[CH:18]([NH2:25])[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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Add 5.0 g of 1-benzhydryl-2-benzimidoylazetidine to an ice cold suspension of 1.16 g of lithium aluminium hydride in 135 ml of dry ether. Stir the mixture at 0° C. for 15 minutes, then allow the mixture to warm to room temperature and continue stirring for 18 hours. Cool the suspension to 0° C. and cautiously quench by the successive addition of 1.25 ml of water, 1.75 ml of 10% aqueous sodium hydroxide, and 3.5 ml of water. Stir, filter and wash the precipitate with ether. Combine the ether washes with the original filtrate and wash the resultant solution successively with water and brine. Dry over anhydrous sodium sulfate, and remove ether in vacuo.
Workup
- temperatureto warm to room temperature
- stirringcontinue stirring for 18 hours
- temperatureCool the suspension to 0° C.
- customcautiously quench by the successive addition of 1.25 ml of water, 1.75 ml of 10% aqueous sodium hydroxide, and 3.5 ml of water
- stirringStir
- filtrationfilter
- washwash the precipitate with ether
- washwash the resultant solution successively with water and brine
- dry with materialDry over anhydrous sodium sulfate
- customremove ether in vacuo
Sources & evidence
- ORD record
- ord-28d1cf979ff5437eb1716032a7829c95
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04140780
Reaction notes
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