1-Benzyl-4-piperidone → HCID 70195907, compound

HRID 343913Notes

Reaction equation

HRID 343913 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:15]=[C:16]1[NH:20][C@H:19]([CH2:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[CH:25]3)[CH2:18][O:17]1>C(O)(=O)C>[OH2:14].[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([C:25]2[C:24]3[C:28](=[CH:29][CH:30]=[C:22]([CH2:21][C@@H:19]4[CH2:18][O:17][C:16](=[O:15])[NH:20]4)[CH:23]=3)[NH:27][CH:26]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 53919389HCID 53919389, compound

Product 1

HCID 70195907HCID 70195907, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Benzyl-4-piperidone (Aldrich, 2.8 g) was added to a stirred suspension of (R)-5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indole (1.0 g), the immediate precursor of the product of Synthetic Example 16, in glac. acetic acid (20 ml) and stirred at 100° C. for 3 hours. The cooled mixture was evaporated in vacuo and the residue taken up in methanol, basified with NH4OH and evaporated in vacuo to give a dark tar. The latter was eluted through a silica column using DCM/EtOH/NH4OH (100:8:1) as eluant and treated with DCM. The resulting precipitate was filtered off to give the desired product as yellow crystals (0.25 g), mp 169°-170.5° C. Elemental analysis and 1H NMR were consistent with the proposed structure.

Workup

  1. customThe cooled mixture was evaporated in vacuo
  2. customevaporated in vacuo
  3. customto give a dark tar
  4. washThe latter was eluted through a silica column
  5. additiontreated with DCM
  6. filtrationThe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-235046021f374314bd36621f1ccc8cd2
Source dataset
uspto-grants-1999_01
Patent number
US05863935

Reaction notes

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