benzyl 4-[4-[3-(4-acetylpiperazin-1-yl)propoxy]phenyl]-5,6-dihydropyridine-1(2H)-carboxylate → 4-[4-[3-(4-Acetylpiperazin-1-yl)propoxy]phenyl]piperidine

HRID 2381089Notes

Reaction equation

HRID 2381089 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH2:25][CH2:24][N:23](C(OCC4C=CC=CC=4)=O)[CH2:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>[Pd].C(O)(C)C.CO.C(Cl)Cl>[NH3:4].[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[CH:18][CH:19]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 1

HCID 68500054benzyl 4-[4-[3-(4-acetylpiperazin-1-yl)propoxy]phenyl]-5,6-dihydropyridine-1(2H)-carboxylate

Product 2

HCID 222AmmoniaYield 10%HCID 685041394-[4-[3-(4-Acetylpiperazin-1-yl)propoxy]phenyl]piperidineYield 152.9%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

Benzyl 4-[4-[3-(4-acetylpiperazin-1-yl)propoxy]phenyl]-5,6-dihydropyridine-1(2H)-carboxylate (17 g, 35.59 mmol) and 5% palladium on carbon (3.37 g, 31.68 mmol) in iso-propanol (170 mL) were stirred under an atmosphere of hydrogen at 5 bar and 40° C. for 2 hours. The reaction mixture was filtered through diatomaceous earth, washing through with iso-propanol. The combined organics were evaporated to dryness to give crude product, which was purified by silica gel chromatography eluting with 0-10% MeOH in DCM, then 10% 7M ammonia in methanol in DCM, to give 4-[4-[3-(4-acetylpiperazin-1-yl)propoxy]phenyl]piperidine (9.4 g, 27.2 mmol, 76%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washwashing through with iso-propanol
  3. customThe combined organics were evaporated to dryness
  4. customto give crude product, which
  5. customwas purified by silica gel chromatography
  6. washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-b56b2272ff484e11b412ab75c264f005
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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