Phenethylamine → 5-chloro-2-methoxy-N-(2-phenylethyl)benzamide

HRID 2266401Notes

Reaction equation

HRID 2266401 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15]([CH:19]=1)[C:16](O)=[O:17].C(N(CC)CC)C.F[B-](F)(F)F.C(OC(C(=NOC(N(C)C)=[N+](C)C)C#N)=O)C>CN(C)C=O.C(OCC)(=O)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15]([CH:19]=1)[C:16]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:17]

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 769705-Chloro-o-anisic acidHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 1185755-chloro-2-methoxy-N-(2-phenylethyl)benzamideYield 90.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.0 g phenethylamine, 5.0 g 5-chloro-2-methoxy-benzoic acid, and 2.72 ml triethylamine were dissolved in 100 ml dimethylformamide. 8.80 g O-((Ethoxycarbonyl)cyanomethyleneamino)-N,N,N′,N′-tetramethyluronium tetrafluoroborate were added portionwise. The reaction mixture is stirred at room temperature for three hours. 300 ml ethyl acetate were added and the mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine. The organic phase was dried over MgSO4 and then the solvent was removed in vacuo to obtain 6.5 g 5-Chloro-2-methoxy-N-phenethyl-benzamide.

Workup

  1. washthe mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1e9175463bb945c39c9c4b4ecdec82de
Source dataset
uspto-grants-2010_12
Patent number
US07858647B2

Reaction notes

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