1-Benzyl-4-piperidone → HCID 15402477, compound

HRID 1487310Notes

Reaction equation

HRID 1487310 reaction equation
[C:1]1([C@@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1C=CC=CC=1.O>[CH2:10]([N:17]1[CH2:22][CH2:21][C:20](=[N:9][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 758181-Phenethylamine, (-)-

Product 1

HCID 15402477HCID 15402477, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of (S)-1-phenylethanamine (1.921 g, 15.85 mmol) in benzene (8.81 ml) were added molecular sieves in water and 1-benzylpiperidin-4-one (2.50 g, 13.21 mmol). The reaction was stirred at room temperature for 5 hrs. The product mixture was filtered and concentrated under reduced pressure to give a yellow oil, which was standing under vacuum at 45° C. for 14 hrs to remove the residual reactant, yielding (S)—N-(1-benzylpiperidin-4-ylidene)-1-phenylethanamine (3.24 g, 11.08 mmol, 84.0% yield) as a yellow oil. 1H NMR (400 MHz, methanol-d4) δ 7.33-7.25 (m, 10H), 4.81-4.76 (m, 1H), 3.54 (s, 2H), 2.72-2.33 (m, 8H), 1.47 (d, J=6.6 Hz, 3H). LCMS (Method E) m/z 291.3 ([M+H]+).

Workup

  1. filtrationThe product mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customto give a yellow oil, which
  4. waitwas standing under vacuum at 45° C. for 14 hrs
  5. customto remove the residual reactant

Sources & evidence

ORD record
ord-40391d09081e4609b7383d78e84f6bf9
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

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