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Butyl bromide → 4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-2-butoxy-5-chlorobenzamide

HRID 1608203
Notes
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Reaction equation

HRID 1608203 reaction equation
[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11]2)=[O:7])=[C:4]([OH:26])[CH:3]=1.[CH2:27](Br)[CH2:28][CH2:29][CH3:30]>[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11]2)=[O:7])=[C:4]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 8002Butyl bromideHCID 148819784-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-hydroxybenzamide

Product 1

HCID 148819104-amino-N-[(4-benzyl-2-morpholinyl)methyl]-2-butoxy-5-chlorobenzamideYield 119.6%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344
Dichloromethane
Solvent
HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-hydroxybenzamide (4.0 g) in 1N aqueous sodium hydroxide solution (32 ml), tetrabutylammonium bromide (3.4 g) and a solution of butyl bromide (4.3 g) in dichloromethane (32 ml) are added. The reaction mixture is stirred at 25° C. for 15 hours and concentrated under reduced pressure. To the residue is added ethyl acetate. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated under reduced pressure. The residue is chromatographed on silica gel with methanol-chloroform (5:95) to give the title compound (5.5 g) as an oil. The free base thus obtained is dissolved in hot ethanol (20 ml), and fumaric acid (1.5 g) is added. The solution is stirred for some time. The precipitate is collected and recrystallized from ethanol to give the fumarate hemihydrate (4.6 g) of the title compound, mp 188°-190° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue is added ethyl acetate
  3. washThe organic layer is washed successively with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with methanol-chloroform (5:95)

Sources & evidence

ORD record
ord-97fe459743bc434899e871f1528483df
Source dataset
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04870074

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes