(E)-2-((1-benzylpiperidin-4-yl)methylene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one → HCID 117940161, compound

HRID 2199792Notes

Reaction equation

HRID 2199792 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[C:15]2/[C:16](=[O:32])[C:17]3[C:22]([CH2:23]/2)=[CH:21][C:20]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[C:19]([O:30][CH3:31])[CH:18]=3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH:15]2[CH2:23][C:22]3[C:17](=[CH:18][C:19]([O:30][CH3:31])=[C:20]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:21]=3)[C:16]2=[O:32])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 117940242(E)-2-((1-benzylpiperidin-4-yl)methylene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 117940161HCID 117940161, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 22 (85 mg, 0.195 mmol) was dissolved in methanol 25 mL, added Pd/C 40 mg and stirred under hydrogen balloon for 6 h. The reaction was filtered through celite bed and washed with excess methanol. The organic layer was concentrated to get the crude compound 23. The crude material was purified by flash chromatography using 100-200 mesh silica gel. The compound was eluted with 20% ethyl acetate in hexane to give half white coloured solid compound 2-((1-benzylpiperidin-4-yl)methyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 23. 1HNMR (400 MHz, CDCl3) δ ppm 7.31 (m, 5H), 7.15 (bs, 1H), 6.85 (bs, 1H), 3.88 (m, 7H), 3.51 (bs, 2H), 3.22 (m, 4H), 2.90 (m, 2H), 2.65 (m, 2H), 1.90 (m, 3H), 1.64 (m, 2H), 1.58 (bs, 4H); MS (ESI) m/z 435.2 (M+H).

Workup

  1. filtrationThe reaction was filtered through celite bed
  2. washwashed with excess methanol
  3. concentrationThe organic layer was concentrated
  4. customto get the crude compound 23
  5. customThe crude material was purified by flash chromatography
  6. washThe compound was eluted with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c592f25be48845e1ae8943eb7145c2ee
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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