Resorcinol → 1,2,3,4-Tetrahydro-8-hydroxy-3-(phenylmethyl)5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 851194Notes

Reaction equation

HRID 851194 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].Cl.[CH2:10]([N:17]1[CH2:22][CH2:21][C:20](=O)[CH:19]([C:24](OCC)=[O:25])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[OH:2][C:1]1[CH:8]=[CH:7][C:6]2[C:20]3[CH2:21][CH2:22][N:17]([CH2:10][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH2:18][C:19]=3[C:24](=[O:25])[O:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 5054ResorcinolHCID 102623Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride

Product 1

HCID 133817811,2,3,4-Tetrahydro-8-hydroxy-3-(phenylmethyl)5H-[1]benzopyrano[3,4-c]pyridin-5-one

Procedure

Prepared by the method described for Example 1 from resorcinol (22 g, 0.2 moles) and 1-benzyl-3-carbethoxy-4-piperidone hydrochloride (59.6 g, 0.2 moles). The product (55 g) is converted to 1,2,3,4-tetrahydro-3-(phenylmethyl)-8-[(1-phenyl-1H-tetrazol-5-yl)oxy]-5H-[1]benzopyrano [3,4-c]pyridin-5-one without further purification.

Workup

  1. customPrepared by the method
  2. customThe product (55 g) is converted to 1,2,3,4-tetrahydro-3-(phenylmethyl)-8-[(1-phenyl-1H-tetrazol-5-yl)oxy]-5H-[1]benzopyrano [3,4-c]pyridin-5-one without further purification

Sources & evidence

ORD record
ord-7fbe1d0a18d74ccd9b590f0577de2ff7
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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