1-Phenethylamine → 2-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-N-(1-phenyl-ethyl)-acetamide

HRID 1528748Notes

Reaction equation

HRID 1528748 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][C:15]([OH:17])=O)=[CH:4][CH:3]=1.[CH3:18][CH:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][C:15]([NH:26][CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:18])=[O:17])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 74081-PhenethylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66577233[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetic acid

Product 1

HCID 665786022-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-N-(1-phenyl-ethyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetic acid (0.154 g, 0.52 mmol), α-methylbenzylamine (0.07 mL, 0.52 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.120 g, 0.62 mmol), 1-hydroxybenzotriazole (0.087 g, 0.62 mmol), and triethylamine (0.22 mL, 1.56 mmol) were combined in CH2Cl2 (1.5 mL). The reaction was stirred at room temperature for 2.5 hours. After aqueous workup the crude material was purified by silica gel chromatography (0-60% EtOAc in hexanes) to give the title compound.

Workup

  1. customAfter aqueous workup the crude material was purified by silica gel chromatography (0-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8f12b3af8e19438dbf1bb375744933a7
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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