Hydrochloric Acid → 1-Methyl-4-[1-(4-nitro-phenyl)-piperidin-3-ylmethyl]-piperazine
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[CH2:11]2)=O)[CH2:4][CH2:3]1.B.[CH2:26]1[CH2:30]OCC1.Cl.C([O-])(O)=O.[Na+]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[CH2:11]2)[CH2:6][CH2:7]1.[CH3:1][N:2]1[CH2:26][CH2:30][N:5]([CH2:6][CH:15]2[CH2:10][CH2:11][N:12]([C:16]3[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)[CH2:13][CH2:14]2)[CH2:4][CH2:3]1Participants
7
Reactant 5
Product 2
Procedure
1-Methyl-4-[1-(4-nitro-phenyl)-piperidin-3-ylmethyl]-piperazine was prepared by warming (4-Methyl-piperazin-1-yl)-[1-(4-nitro-phenyl)-piperidin-3-yl]-methanone of Example 443a with borane.THF (10 equivalents) at 60° C. for 16 hours, followed by a standard aqueous HCl workup. The resulting aqueous phase was neutralized with NaHCO3 and extracted with EtOAc (2×). The organics were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to give 1-Methyl-4-[1-(4-nitro-phenyl)-piperidin-4-ylmethyl]-piperazine as an orange oil, which was used for subsequent step without further manipulation. LC/MS (E/I+) 319.18 (M+H).
Workup
- extractionextracted with EtOAc (2×)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ca31101ff3cf4f12b285fede964a4886
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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