3-(4-Chlorophenyl)propan-1-amine → HCID 14011765, compound

HRID 986216

Reaction equation

HRID 986216 reaction equation
[NH2:1][C:2]1[O:3][C:4]([C:7](=O)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][N:6]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][NH2:25])=[CH:18][CH:17]=1>O.C(O)(C)(C)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][NH:25][C:2]2[N:1]=[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:4]([OH:3])=[CH:5][N:6]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 64857723-(4-Chlorophenyl)propan-1-amineHCID 13906322HCID 13906322, compound

Product 1

HCID 14011765HCID 14011765, compoundYield 4.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

2-Amino-5-benzoyloxazole (3.0 g, 16 mmol) was combined with p-chlorophenylpropylamine (2.7 g, 16 mmol) in 15 ml of water and t-butanol (2:1) and heated under reflux in nitrogen for 16 hours. The solvents were removed in a vacuum, and the residue was treated with hot acetonitrile and filtered. After concentration in vacuum, the filtrate was chromatographed on silica gel using hexane and ethyl acetate (1:1) as eluent to give 0.24 mg (4.4%) of the title compound as an oil. NMR (CDCl3): 1.8-2.0 (m, 2H), 2.4-2.7 (m, 2H), 3.1-3.4 (m, 2H), 5.0 (b s, 1H), 7.0-7.5 (m, 7H), 7.8 (s, 1H), 7.9-8.0 (m, 2H).

Workup

  1. temperatureheated
  2. temperatureunder reflux in nitrogen for 16 hours
  3. customThe solvents were removed in a vacuum
  4. additionthe residue was treated with hot acetonitrile
  5. filtrationfiltered
  6. concentrationAfter concentration in vacuum
  7. customthe filtrate was chromatographed on silica gel

Sources & evidence

ORD record
ord-03fae8e6050a4bc6b5705e3aec45991d
Source dataset
uspto-grants-1987_12
Patent number
US04711888

Linked notes

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