3-Methylbutanal → HCID 21345775, compound
Reaction equation
[CH2:1]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH:3](C)C.[N+](C1C=CC(N2CCNCC2)=CC=1)([O-])=O.C(=O)CC(C)C>>[N+:18]([C:15]1[CH:14]=[CH:13][C:12]([N:9]2[CH2:8][CH2:7][N:6]([CH2:1][CH2:2][CH3:3])[CH2:11][CH2:10]2)=[CH:17][CH:16]=1)([O-:20])=[O:19]Participants
Procedure
Following the general procedure described above for the synthesis of 1-isopentyl-4-(4-nitrophenyl)piperazine, treatment of 1-(4-nitrophenyl)piperazine (5.00 g, 24.1 mmol, 1.0 eq) with isovaleraldehyde (4.16 g, 5.18 mL, 48.3 mmol, 3 eq) at RT for 48 h provided the title compound as a yellow solid (5.34 g, 89% recovery, 93% purity as determined by LC/MS analysis @ UV 254 nm detection). In this case, upon addition of hexane (25 mL) to the crude residue, obtained from evaporation of the DCM extract, and stirring for 24 h the product precipitated from solution, was collected by filtration, washed with hexanes (2×25 ml), and was dried under vacuum. The crude product is used in the next step without further purification. LCMS-ESI (m/z): calcd for C13H19N3O2, 249; [M+H]+ found, 250.
Sources & evidence
- ORD record
- ord-1323449e869b4d5c9a2cbf09c0c54563
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977352B2
Reaction notes
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