Hydrochloric Acid → 1-Methyl-4-[1-(4-nitro-phenyl)-piperidin-4-ylmethyl]-piperazine

HRID 1262041Notes

Reaction equation

HRID 1262041 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=O)[CH2:4][CH2:3]1.B.C1COCC1.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][N:13]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:7]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 66712189(4-Methyl-piperazin-1-yl)-[1-(4-nitro-phenyl)-piperidin-4-yl]-methanone

Product 1

HCID 667117331-Methyl-4-[1-(4-nitro-phenyl)-piperidin-4-ylmethyl]-piperazine

Procedure

1-Methyl-4-[1-(4-nitro-phenyl)-piperidin-4-ylmethyl]-piperazine was prepared by warming (4-Methyl-piperazin-1-yl)-[1-(4-nitro-phenyl)-piperidin-4-yl]-methanone of Example 444a 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 solid, which was used for subsequent step without further manipulation. LC/MS (E/I+) 319.15 (M+H).

Workup

  1. custom1-Methyl-4-[1-(4-nitro-phenyl)-piperidin-4-ylmethyl]-piperazine was prepared
  2. extractionextracted with EtOAc (2×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7af61e920db44fab8959fa408679b6df
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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