1-(Bromomethyl)-3-chlorobenzene → [2-(3-Chloro-benzylamino)-5-methoxy-phenyl]-(4-isopropyl-phenyl)-methanone

HRID 445153Notes

Reaction equation

HRID 445153 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=1)=[O:11].C(N(CC)C(C)C)(C)C.[Cl:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34]Br>ClCCl>[Cl:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34][NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 81531DiisopropylethylamineHCID 45139626(2-Amino-5-methoxy-phenyl)-(4-isopropyl-phenyl)-methanone

Product 1

HCID 60112864[2-(3-Chloro-benzylamino)-5-methoxy-phenyl]-(4-isopropyl-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg (0.327 mmol) (2-amino-5-methoxy-phenyl)-(4-isopropyl-phenyl)-methanone in 1 ml dichloromethane is added 140 μl (0.818 mmol) N,N-diisopropyl-ethylamine and 48.7 μl (0.360 mmol)3-chloro-benzyl bromide. The reaction mixture is heated under reflux for 4 days and extracted with water/dichloromethane. The organic residue is chromatographed. For further purification the corresponding hydrochloride is precipitated form an etheric solution by addition of gaseous hydrochloric acid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 4 days
  3. extractionextracted with water/dichloromethane
  4. customThe organic residue is chromatographed
  5. customFor further purification the corresponding hydrochloride
  6. customis precipitated form an etheric solution
  7. additionby addition of gaseous hydrochloric acid

Sources & evidence

ORD record
ord-427712d4b5aa4eeead56e030c6865087
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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