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Water → N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(4-acetamidophenoxy)-propanamine

HRID 1656647
Notes
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Reaction equation

HRID 1656647 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[C:12]([NH:15][C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][CH:22]2[O:24][CH2:23]2)=[CH:18][CH:17]=1)(=[O:14])[CH3:13].O>CS(C)=O>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][CH2:11][CH:2]1[NH:1][CH2:23][CH:22]([OH:24])[CH2:21][O:20][C:19]1[CH:25]=[CH:26][C:16]([NH:15][C:12](=[O:14])[CH3:13])=[CH:17][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 346772-AminotetralinHCID 2798712N-(4-((oxiran-2-yl)methoxy)phenyl)acetamide

Product 1

HCID 19788327N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(4-acetamidophenoxy)-propanamineYield 35.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-aminotetralin (2.5 g) and 1-(4-acetamidophenoxy)-2,3-epoxypropane (3.52 g) in dimethylsulfoxide (40 ml) is heated at 80° C. for 5 hours. The reaction mixture is allowed to cool toat room temperature and water (180 ml) is then added thereto. The precipitate which forms is recovered by filtration and crystallized from absolute ethanol (120 ml) yielding 2.15 g of N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(4-acetamidophenoxy)-propanamine; m.p. 133°-136° C.

Workup

  1. temperatureto cool toat room temperature
  2. filtrationThe precipitate which forms is recovered by filtration
  3. customcrystallized from absolute ethanol (120 ml)

Sources & evidence

ORD record
ord-3f73e23a7264437daa68db8f0162658b
Source dataset
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05254595

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes