Phenylacetaldehyde → 3-[4-(Phenethyl-amino)-phenyl]-propionic acid ethyl ester

HRID 1944537Notes

Reaction equation

HRID 1944537 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.[CH2:19]([O:21][C:22](=[O:32])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)[CH3:20].[C:33]1([CH2:39][CH:40]=O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[OH-].[NH4+]>ClCCCl.O>[CH2:19]([O:21][C:22](=[O:32])[CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([NH:31][CH2:40][CH2:39][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:30]=1)[CH3:20]

Participants

7

Reactant 4

HCID 998PhenylacetaldehydeHCID 14923Ammonium HydroxideHCID 10442595Ethyl 3-(4-aminophenyl)propanoateHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)

Product 1

HCID 598598723-[4-(Phenethyl-amino)-phenyl]-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

Tetramethylammonium triacetoxyborohydride (4.9 g, 18.6 mmol) was added to a solution of 3-(4-aminophenyl)-propionic acid ethyl ester (3.0 g, 15.5 mmol) and phenylacetaldehyde (1.08 mL, 15.5 mmol) in 1,2-dichloroethane (50 mL). The resultant solution was stirred at room temperature for ten minutes, then heated at reflux overnight. The solution was treated with a 1:1 solution of water:ammonium hydroxide. The organic layer was applied to a silica gel column and eluted with ethyl acetate/hexane ( 1/9) to give the product as an oil, 1.3 g (28%). MS: m/z 298 (MH+). 1H NMR (CDCl3): δ 1.24 (t, 3 H), 2.58 (t, 2 H), 2.86 (s, 3 H), 3.53 (t, 2 H), 3.67 (t, 2 H), 4.13 (q, 2 H), 4.32 (t, 2 H), 6.67 (d, 2 H), 7.09 (d, 2 H), 7.19-7.32 (m, 5 H).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. washeluted with ethyl acetate/hexane ( 1/9)

Sources & evidence

ORD record
ord-370503acbac94f06b46f327d78e11075
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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