Piperidine → (4-Benzylamino-phenyl)-piperidin-1-yl-methanone

HRID 2380967Notes

Reaction equation

HRID 2380967 reaction equation
[CH2:1]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.Cl.C(N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>C(#N)C.O>[CH2:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8082PiperidineHCID 8471TriethylamineHCID 8535464-(benzylamino)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178526939HCID 178526939, compound

Product 1

HCID 67130556(4-Benzylamino-phenyl)-piperidin-1-yl-methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 4-(benzylamino)benzoic acid (200 mg, 0.88 mmol) in acetonitrile (2 ml) was added piperidine (0.174 ml, 1.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (184 mg, 0.97 mmol), hydroxybenzotriazole hydrate (10 mg, catalytic) followed by triethylamine (0.31 ml, 2.2 mmol) and the reaction was stirred at room temperature for 16 hours. The reaction mixture was diluted with water (2 ml) and extracted with dichloromethane (2×2 ml). The organic phases were combined, washed with brine, dried over magnesium sulfate and then concentrated in vacuo. The residue was purified by flash column chromatography (SiO2) eluting with ethyl acetate/dichloromethane (1:4) to afford the title compound as an off white solid (122 mg, 47% yield).

Workup

  1. extractionextracted with dichloromethane (2×2 ml)
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2)
  6. washeluting with ethyl acetate/dichloromethane (1:4)

Sources & evidence

ORD record
ord-478b7767e245437aa82144000540f4fc
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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