Ethylamine → N-ethyl-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetamide
Reaction equation
[CH3:1][N:2]1[CH2:21][CH2:20][C:5]2[N:6]([CH2:14][C:15]([O:17]CC)=O)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[CH2:22]([NH2:24])[CH3:23]>>[CH2:22]([NH:24][C:15](=[O:17])[CH2:14][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=2[C:4]2[CH2:3][N:2]([CH3:1])[CH2:21][CH2:20][C:5]1=2)[CH3:23]Participants
3
Conditions
- Temperature
- 120 °C
Procedure
A mixture of ethyl 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetate (100 mg) and ethylamine (1 ml) was heated at 120° C. for 15 h to obtain N-ethyl-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetamide (CD23) after purification on neutral alumina chromatography eluting with methanol-dichloromethane gradient. The free base was converted into its oxalate salt by treatment of oxalic acid (1 equiv) in anhydrous THF.
Sources & evidence
- ORD record
- ord-9158444af29b4405869b2195b77556e8
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115137B2
Reaction notes
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