1-(4-Amino-3,5-dichlorophenyl)-2-bromoethan-1-one → HCID 70451844, compound

HRID 1381274Notes

Reaction equation

HRID 1381274 reaction equation
[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][C:3]=1[Cl:13].[CH3:14][C@@H:15]([NH2:27])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([NH2:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([CH:6]([OH:9])[CH2:7][N:27]([CH2:7][CH:6]([OH:9])[C:5]2[CH:4]=[C:3]([Cl:13])[C:2]([NH2:1])=[C:11]([Cl:12])[CH:10]=2)[C@H:15]([CH3:14])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([NH2:26])=[O:25])=[CH:20][CH:19]=2)=[CH:4][C:3]=1[Cl:13]

Participants

4

Reactant 2

HCID 30158971-(4-Amino-3,5-dichlorophenyl)-2-bromoethan-1-oneHCID 54361161HCID 54361161, compound

Product 1

HCID 70451844HCID 70451844, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 13.6 g of 4-amino-3,5-dichlorophenacyl bromide and 4.6 g of (R)-1-methyl-3-(4-aminocarbonylphenyl)propylamine in 100 ml of chloroform was warmed to 50° for 3 hours. The mixture was evaporated in vacuo, the residue was dissolved in 200 ml of methanol was 70 ml of water and a solution of 3.0 g of sodium borohydride in 20 ml of water was added dropwise thereto while cooling with ice and stirring so that the temperature did not rise above 20°. After completion of the addition, the mixture was stirred at 5°-10° for a further 2 hours, then poured into ice-water and extracted with methylene chloride. The material isolated from the methylene chloride extract was chromatographed on silica gel. With chloroform/n-propanol/25% ammonia (1000:10:1) there was obtained pure p-[(R)-3-[bis-[(RS)-4-amino-3,5-dichloro-β-hydroxyphenethyl]amino]butyl]benzamide in amorphous form; [α]D20 =-46° (c=1.0% in methanol); ε242 =31080; ε302 =7250.

Workup

  1. temperaturewas warmed to 50° for 3 hours
  2. customThe mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in 200 ml of methanol
  4. additiona solution of 3.0 g of sodium borohydride in 20 ml of water was added dropwise
  5. temperaturewhile cooling with ice
  6. customdid not rise above 20°
  7. additionAfter completion of the addition
  8. stirringthe mixture was stirred at 5°-10° for a further 2 hours
  9. additionpoured into ice-water
  10. extractionextracted with methylene chloride
  11. customThe material isolated from the methylene chloride
  12. extractionextract
  13. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-5c40968b670c42a584a7584dc359db0e
Source dataset
uspto-grants-1986_04
Patent number
US04585796

Reaction notes

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