Bromomethylcyclopropane → 1-(4-(Cyclopropylmethoxy)benzyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one

HRID 594626Notes

Reaction equation

HRID 594626 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[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[C:15](=[O:25])[CH2:14][CH2:13][CH2:12]1.Br[CH2:27][CH:28]1[CH2:30][CH2:29]1>>[CH:28]1([CH2:27][O:24][C:21]2[CH:22]=[CH:23][C:18]([CH2:17][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:25])=[CH:19][CH:20]=2)[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 690817446-(2,6-Dimethoxyphenyl)-1-(4-hydroxybenzyl)piperidin-2-one

Product 1

HCID 690845921-(4-(Cyclopropylmethoxy)benzyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one

Procedure

Prepared according to the described general procedure 7 (GP7) by O-alkylation of 6-(2,6-dimethoxyphenyl)-1-(4-hydroxybenzyl)piperidin-2-one with commercially available (bromomethyl)cyclopropane. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions E): tR=0.78 min.; [M+H]+: 396.27 g/mol.

Workup

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

Sources & evidence

ORD record
ord-b0158c0308974fbbb053e53e76029325
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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