Sodium Hydroxide → N-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]-2-(2-chloro-3,4-dimethoxyphenyl)ethylamine

HRID 486376Notes

Reaction equation

HRID 486376 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][NH:14][C:15](=O)[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[OH:17].[OH-].[Na+]>C1(C)C=CC=CC=1>[OH:17][CH:16]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[CH2:15][NH:14][CH2:13][CH2:12][C:3]1[CH:4]=[CH:5][C:6]([O:10][CH3:11])=[C:7]([O:8][CH3:9])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13697589N-(2-chloro-3,4-dimethoxyphenylethyl)-4-methoxymandelamide

Product 1

HCID 3018199N-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]-2-(2-chloro-3,4-dimethoxyphenyl)ethylamineYield 77.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

10.58 g of N-(2-chloro-3,4-dimethoxyphenylethyl)-4-methoxymandelamide was dissolved in 105.8 ml of toluene. A solution of 16.5 ml of Vitrite in 16.5 ml of toluene was added dropwise to the solution at room temperature. Then the reaction was conducted at 50° C. for 4 hours. After cooling, 100 ml of a 10% NaOH solution was added dropwise thereto and the mixture was left to stand overnight. Crystals thus formed were separated by filtration, washed with water and dried to obtain 7.87 g (yield: 77.2%) of N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-2-(2-chloro-3,4-dimethoxyphenyl)ethylamine.

Workup

  1. temperatureAfter cooling
  2. waitthe mixture was left
  3. waitto stand overnight
  4. customCrystals thus formed
  5. customwere separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-faf1dc85e1e34644a7ae2559847a6ac4
Source dataset
uspto-grants-1994_03
Patent number
US05292521

Reaction notes

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