2-(4-Chlorophenyl)ethylamine → Methyl (4-{[2-(4-chlorophenyl)ethyl]carbamoyl}phenyl)acetate

HRID 1256942Notes

Reaction equation

HRID 1256942 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][NH2:48])=[CH:42][CH:41]=1>C(#N)C.C(N(CC)C(C)C)(C)C>[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][NH:48][C:9]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:14])=[CH:13][CH:12]=2)=[O:11])=[CH:42][CH:41]=1

Participants

6

Reactant 3

HCID 674302-(4-Chlorophenyl)ethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 138161444-(2-Methoxy-2-oxoethyl)benzoic acid

Product 1

HCID 86659540Methyl (4-{[2-(4-chlorophenyl)ethyl]carbamoyl}phenyl)acetate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 4-(2-methoxy-2-oxoethyl)benzoic acid (1.00 g) in acetonitrile (50 ml), N,N-diisopropyl ethyl amine (2.63 ml), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (2.94 g) and 2-(4-chlorophenyl)ethylamine (790 ml) were added, and the mixed solution was stirred at room temperature for 16 hours. The solvent was removed by evaporation under reduced pressure, and the resulting crude product was purified by column chromatography (neutral OH type silica gel, ethyl acetate/n-hexane=30 to 50%) to give methyl (4-{[2-(4-chlorophenyl)ethyl]carbamoyl}phenyl)acetate (2.02 g).

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe resulting crude product was purified by column chromatography (neutral OH type silica gel, ethyl acetate/n-hexane=30 to 50%)

Sources & evidence

ORD record
ord-7740787c91a0493ab5296f4bbfac262a
Source dataset
uspto-grants-2013_06
Patent number
US08461329B2

Reaction notes

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