3-(4-Hydroxyphenyl)propionic acid → HCID 68871483, compound

HRID 2112032Notes

Reaction equation

HRID 2112032 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:2].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21](O)=[O:22])=[CH:15][CH:14]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.CCOC(C)=O>[CH2:1]([N:3]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[C:21](=[O:22])[CH2:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=1)[CH3:2]

Participants

7

Reactant 4

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 80553N-Ethylpyridine-2-ethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 68871483HCID 68871483, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N-Ethyl-N-(2-pyridin-2-ylethyl)amine (0.5 g, 3.32 mmol) and 3-(4-hydroxyphenyl)-propanoic acid (0.50 g, 3.00 mmol) was dissolved in dimethylformamide (5 ml) and cooled to 0° C. N-[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate (1.18 g, 3.66 mmol) and diisopropylethylamine (0.90 g, 7.0 mmol) were added and the solution was warmed to room temperature and stirred overnight. EtOAc (15 ml) was added and the organic phase was washed with two portions of sodium hydrogencarbonate (aq, 10 ml). The organic phase was dried MgSO4) and EtOAc was removed by evaporation to give 0.913 gram of N-ethyl-3-(4 hydroxyphenyl)-N-(2-pyridin-2-ylethyl)propanamide (yield 91.9%).

Workup

  1. temperaturethe solution was warmed to room temperature
  2. washthe organic phase was washed with two portions of sodium hydrogencarbonate (aq, 10 ml)
  3. customwas removed by evaporation

Sources & evidence

ORD record
ord-3bc9ed144d5f456c8199fe696fff687d
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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