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

HRID 62237Notes

Reaction equation

HRID 62237 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-45590e4790474960b67a6d39473c31c4
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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