Phenylethanolamine → N-(2-(4-Methylphenoxy)-1-methylethyl)-2-hydroxy-2-phenylethanamine

HRID 280317Notes

Reaction equation

HRID 280317 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][NH2:4].[CH3:11][C:12]1[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18](=O)[CH3:19])=[CH:14][CH:13]=1>>[CH3:11][C:12]1[CH:22]=[CH:21][C:15]([O:16][CH2:17][CH:18]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:19])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 1000PhenylethanolamineHCID 81195p-Tolyloxyacetone

Product 1

HCID 23322170N-(2-(4-Methylphenoxy)-1-methylethyl)-2-hydroxy-2-phenylethanamine

Procedure

The title compound was prepared in the manner described in Example 3 using 2-hydroxy-2-phenylethanamine and (4-methylphenoxy)propan-2-one. Recrystallization from heptane gave the title compound m.p. 87-105. τ(CDCL3) 8.9 (3H, d, J=6 Hz), 7.7 (3H, s), 6.7-7.5 (3H, +2H (disappears with D2O)), 6.2 (2H, m), 5.3 (1H, m), 3.3 (2H, d, J=9 Hz), 2.9 (2H, d, J=9 Hz), 2.7 (5H, m).

Workup

  1. customThe title compound was prepared in the manner
  2. customRecrystallization from heptane

Sources & evidence

ORD record
ord-5c10845c3f5445f58eb062652ec3fce6
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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