Urea → N-[2-(Diethylamino)ethyl]-1H-indole-2-carboxamide
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.O[N:14]1[C:18](=O)[CH2:17][CH2:16][C:15]1=O.[CH:21]1([N:27]=C=NC2CCCCC2)CCCC[CH2:22]1.NC(N)=O>C(OCC)C.C(#N)C>[CH2:15]([N:14]([CH2:22][CH2:21][NH:27][C:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:12])[CH2:18][CH3:17])[CH3:16]Participants
Procedure
To a suspension of 4.83 g indol-2-carboxylic acid and 3.8 g N-hydroxy-succinimide in 60 ml abs. acetonitrile is added at room temperature a solution of 6.8 g dicyclohexyl-carbodiimide in 30 ml abs. diethyl ether, whereby the temperature rises rapidly to 33°. The suspension goes into solution and urea precipitates. The mixture is stirred at room temperature for 3 hours, filtered and the filtrate washed with acetonitrile. The filtrate is treated dropwise with 8.5 ml (60 mM) diethyl-aminoethyl amine, whereby the temperature rises from 20° to 28°. The mixture is left overnight and then is partitioned between 1N aqueous sodium carbonate solution and CH2Cl2. The organic phase is evaporated to give the title compound, recrystallised from CH2Cl2 /hexane m.p. 133°-134°.
Workup
- customrises rapidly to 33°
- customprecipitates
- filtrationfiltered
- washthe filtrate washed with acetonitrile
- additionThe filtrate is treated dropwise with 8.5 ml (60 mM) diethyl-aminoethyl amine, whereby the temperature
- customrises from 20° to 28°
- waitThe mixture is left overnight
- customis partitioned between 1N aqueous sodium carbonate solution and CH2Cl2
- customThe organic phase is evaporated
Sources & evidence
- ORD record
- ord-aad2674706c74a949fcb13406733d67c
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05561149
Reaction notes
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