Aluminium lithium hydride → HCID 54206885, compound
Reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[CH2:14][N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])=[CH:7][CH:6]=1)(=O)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([NH:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[CH2:14][N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])=[CH:7][CH:6]=1)[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of the free base of compound 2a (5.0 g) in dry THF (25 ml) was added dropwise to a suspension of 1 g LiAlH4 in dry 50 ml THF at 20°-25° C. The mixture was refluxed for 2 hours, excess LiAlH4 was destroyed by cautiously adding 2 ml diluted aqueous NaOH solution. Inorganic salts were filtered off and the crude 6-ethylamino-1-(N,N-dipropylaminomethyl)indan was isolated as a viscous oil upon evaporation of the solvents. Yield: 3.0 g. All off the thus obtained ethylaminoindan derivative was dissolved in 60 ml dichloromethane and 2.3 ml triethylamine was added. The mixture was cooled to 0° C. and a solution of 1 ml acetylchloride in 10 ml dichloromethane was added dropwise at 5°-10° C. The mixture was stirred for another hour at room temperature. Water (100 ml) was added and the organic phase was subsequently separated and worked up. The remaining oil was dissolved in acetone and oxalic acid was added. The oxalate salt of the title compound 14a crystallized and was filtered off and dried in vacuo. Yield: 2.5 g. Mp: 129°-130° C.
Workup
- temperatureThe mixture was refluxed for 2 hours
- customexcess LiAlH4 was destroyed
- additionby cautiously adding 2 ml diluted aqueous NaOH solution
- filtrationInorganic salts were filtered off
Sources & evidence
- ORD record
- ord-ac1d0f3c157a4e9794ced6a8b59a6d96
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05807889
Reaction notes
Loading…