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

HRID 1656647Notes

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

Participants

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

temperatureto cool toat room temperature
filtrationThe precipitate which forms is recovered by filtration
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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