N,N'-Dimethylethylenediamine → HCID 66711195, compound
Reaction equation
CO[C:3](=[O:15])[CH:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1.[CH3:16][NH:17][CH2:18][CH2:19][NH:20][CH3:21]>>[CH3:16][N:17]1[CH2:18][CH2:19][N:20]([CH3:21])[CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[C:3]1=[O:15]Participants
3
Procedure
1,4-Dimethyl-3-(3-nitro-phenyl)-piperazin-2-one was prepared from bromo-(3-nitro-phenyl)-acetic acid methyl ester and N,N′-dimethyl-ethane-1,2-diamine in an analogous manner to Example 1072b. Product isolated as a clear-orange oil (959 mg, 98%). LCMS (m/e) 250 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.32 (s, 1H), 8.14 (d, 1H, J=8.2 Hz), 7.76 (d, 1H, J=7.6 Hz), 7.54-7.46 (m, 1H), 3.83 (s, 1H), 3.83-3.73 (m, 1H), 3.26-3.18 (m, 1H), 3.08-3.01 (m, 1H), 2.97 (s, 3H), 2.79-2.69 (m, 1H), 2.19 (s, 3H).
Sources & evidence
- ORD record
- ord-55e80bb59b654536b515a9bda8c9cbea
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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