4-(6-Methoxynaphthalen-2-YL)piperidine → (S)-alpha-(2'-(2-hydroxy-3-(4-(6-methoxynaphthalen-2-yl) piperidino) propyloxy) benzylidene)-gamma-butyrolactone

HRID 460667Notes

Reaction equation

HRID 460667 reaction equation
[O:1]1[CH2:18][C@H:2]1[CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[CH:7]=[C:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10].[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[CH:25]=[CH:24]2>CO>[OH:1][C@@H:2]([CH2:18][N:34]1[CH2:33][CH2:32][CH:31]([C:26]2[CH:25]=[CH:24][C:23]3[C:28](=[CH:29][CH:30]=[C:21]([O:20][CH3:19])[CH:22]=3)[CH:27]=2)[CH2:36][CH2:35]1)[CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[CH:7]=[C:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10]

Participants

4

Reactant 2

HCID 227293124-(6-Methoxynaphthalen-2-YL)piperidineHCID 86585643(S)-alpha-(2'-(2,3-epoxypropan-1-yloxy)benzylidene)-gamma-butyrolactone

Product 1

HCID 69498080(S)-alpha-(2'-(2-hydroxy-3-(4-(6-methoxynaphthalen-2-yl) piperidino) propyloxy) benzylidene)-gamma-butyrolactoneYield 42.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-α-(2′-(2,3-Epoxypropan-1-yloxy)benzylidene)-γ-butyrolactone (1.2 g) and 4-(6-methoxynaphthalen-2-yl)piperidine (1.2 g) were dissolved in methanol (50 ml), and the mixture was refluxed under heating for 2 hr. After cooling, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (1.0 g), melting point 148–150° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hr
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-d1d37a4f613a4cd08cf736771faffb97
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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