Phenylethanolamine → 2-chloro-N-(4-(((2-hydroxy-2-phenylethyl)amino)carbonyl)phenyl)benzamide

HRID 1951598Notes

Reaction equation

HRID 1951598 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)=[O:5].Cl.C(N=C=N)C.O.ON1C2C=CC=CC=2N=N1.[NH2:37][CH2:38][CH:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[OH:40].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:37][CH2:38][CH:39]([OH:40])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:13])=[CH:14][CH:15]=1)=[O:5]

Participants

8

Reactant 5

HCID 1000PhenylethanolamineHCID 8471TriethylamineHCID 11329884-(2-Chlorobenzamido)benzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 574653822-chloro-N-(4-(((2-hydroxy-2-phenylethyl)amino)carbonyl)phenyl)benzamideYield 80.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

under an N2 atmosphere, 4-(2-chlorobenzamido)benzoic acid (0.500 g, 1.81 mmol) was dissolved in N,N-dimethylformamide (10.0 ml) and the solution was treated with N-3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.696 g, 3.62 mmol), 1-hydroxybenzotriazole hydrate (0.491 g, 3.62 mmol), 2-amino-1-phenylethanol (0.498 g, 3.62 mmol), and triethylamine (0.506 ml, 3.62 mmol). The reaction was allowed to stir at room temperature overnight. The reaction was diluted with ethyl acetate and washed with 0.5N HCl followed by 5% NaHCO3. The organic layer was dried (Na2SO4), and concentrated in vacuo. The resulting solid was triturated with a mixture of ethyl acetate and hexanes to afford 2-chloro-N-(4-(((2-hydroxy-2-phenylethyl)amino)carbonyl)phenyl)benzamide (0.578 g, 71.5%) after collecting the solid by filtration. ESI m/z=395.0 (M+H+).

Workup

  1. washwashed with 0.5N HCl
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting solid was triturated with a mixture of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-b503c0adfdb8422f8102b52e8cac45d9
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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