5-(Bromomethyl)-2,1,3-benzoxadiazole → 1-(Benzo[c][1,2,5]oxadiazol-5-ylmethyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one

HRID 594588Notes

Reaction equation

HRID 594588 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[NH:16][C:15](=[O:17])[CH2:14][CH2:13][CH2:12]1.Br[CH2:19][C:20]1[CH:28]=[CH:27][C:23]2=[N:24][O:25][N:26]=[C:22]2[CH:21]=1>>[N:24]1[O:25][N:26]=[C:22]2[CH:21]=[C:20]([CH2:19][N:16]3[CH:11]([C:4]4[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])[CH2:12][CH2:13][CH2:14][C:15]3=[O:17])[CH:28]=[CH:27][C:23]=12

Participants

3

Reactant 2

HCID 27355875-(Bromomethyl)-2,1,3-benzoxadiazoleHCID 690825266-(2,6-Dimethoxyphenyl)piperidin-2-one

Product 1

HCID 690838271-(Benzo[c][1,2,5]oxadiazol-5-ylmethyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one

Procedure

Prepared according to the described general procedure 4 (GP4) by reaction of 6-(2,6-dimethoxyphenyl)piperidin-2-one with commercially available 5-(bromomethyl)benzo[c][1,2,5]oxadiazole. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions E): tR=0.74 min.; [M+H]+: 368.1 g/mol.

Workup

  1. customPrepared
  2. customSubsequent purification by preparative HPLC
  3. customafforded the target compound

Sources & evidence

ORD record
ord-3d26f533278a4f6f9d507e664bb60065
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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