3-Amino-1-propanol → HCID 18918916, compound

HRID 1291207Notes

Reaction equation

HRID 1291207 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:22]=[CH:21][C:10]([C:11]([C:13]2[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=2)=[O:12])=[CH:9][CH:8]=1>C(O)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([C:13]2[CH:20]=[CH:19][C:16]([CH2:17][NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[CH:15][CH:14]=2)=[O:12])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 98396514-(4-Chlorobenzoyl)benzyl bromide

Product 1

HCID 18918916HCID 18918916, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-amino-l-propanol (3.00 g) in ethanol (40 ml) was added 4-(4-chlorobenzoyl)benzyl bromide (3.10 g) and the mixture was refluxed for 4.5 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure and the residue was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developed with chloroform: methanol=9:1) to provide the title compound as white powder (1.36 g; yield 45%). 1H-NMR (CDCl3) δ: 1.76(2H,q,J=5.6Hz), 2.29(2H,m), 2.93(2H,t,J=5.6Hz), 3.83(2H,t,J=5.6Hz), 3.90(2H,s), 7.41-7.50(4H,m), 7.71-7.78(4H,m).

Workup

  1. temperaturethe mixture was refluxed for 4.5 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developed with chloroform: methanol=9:1)

Sources & evidence

ORD record
ord-2cb86f692fc04b26bfee1b7055a9d86a
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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