Potassium Carbonate → 2-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-phenyl-acetamide

HRID 560116

Reaction equation

[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)[OH:4].Cl[CH2:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+].OP([O-])(O)=O.[K+]>C(#N)C.C(OCC)(=O)C>[Br:11][C:7]1[CH:6]=[C:5]([CH:3]([OH:4])[CH2:2][NH:1][CH2:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-amino-1-(3-bromo-phenyl)-ethanol (example 33, step 1, 1.34 g) and crude 2-chloro-N-phenyl-acetamide (example 33, step 2, 1.0 g) in acetonitrile (15 mL) was added potassium carbonate (1.03 g). The mixture was heated to 80° C. overnight. A 1M solution of KH2PO4 was added, followed by ethyl acetate. The phases were separated, and the inorganic one was extracted with ethyl acetate (x2). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. Column chromatography (SiO2, CH2Cl2/MeOH 95:5) followed by precipitation from a mixture of diethylether/n-heptane (1:4) gave 2-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-phenyl-acetamide (0.87 g, 42%) as a white solid, MS: 349.1 (M+H, 1Br)+.

Workup

customThe phases were separated
extractionthe inorganic one was extracted with ethyl acetate (x2)
washThe combined organic layers were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customColumn chromatography (SiO2, CH2Cl2/MeOH 95:5) followed by precipitation from a mixture of diethylether/n-heptane (1:4)

Sources & evidence

ORD record: ord-e54f51f2b32547079b951d7506d0e604
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063088B2

Linked notes

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