Benzyl Bromide → (2-Benzylamino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone

HRID 445162Notes

Reaction equation

HRID 445162 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]#[CH:11])=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=[O:13].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[CH2:23]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]#[CH:11])=[CH:4][C:3]=1[C:12]([C:14]1[CH:15]=[CH:16][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:18][CH:19]=1)=[O:13])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 45139628(2-Amino-5-(prop-2-yn-1-yloxy)phenyl)(4-isopropylphenyl)methanone

Product 1

HCID 45140213(2-Benzylamino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 100 mg (0.341 mmol) (2-amino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone, 44.6 μl (0.375 mmol) benzyl bromide and 32 μl (0.375 mmol) N-ethyl-diisopropylamine in 2 ml dioxane is heated at 100° for 90 h. The reaction mixture is concentrated and the residue taken up in 0.1 M sodium hydroxide solution and extracted with dichloromethane. Preparative HPLC affords (2-benzylamino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-867c9a83e870470094a67110dba800cf
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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