4-[2-Hydroxy-3-(propan-2-ylamino)propoxy]phenol → 1-[4-[2-(4-Chlorophenethyloxy)-ethoxy]phenoxy]-3-isopropylamino-2-propanol hydrochloride

HRID 1905979Notes

Reaction equation

HRID 1905979 reaction equation
[CH:1]([NH:4][CH2:5][CH:6]([OH:16])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:3])[CH3:2].CS(O[CH2:22][CH2:23][O:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)(=O)=O>C(OCC)(=O)C>[ClH:33].[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH:6]([OH:16])[CH2:5][NH:4][CH:1]([CH3:3])[CH3:2])=[CH:14][CH:13]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 1823364-[2-Hydroxy-3-(propan-2-ylamino)propoxy]phenolHCID 132108222-[2-(4-Chlorophenyl)ethoxy]ethyl methanesulfonate

Product 1

HCID 132108351-[4-[2-(4-Chlorophenethyloxy)-ethoxy]phenoxy]-3-isopropylamino-2-propanol hydrochlorideYield 114.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a manner analogous to that described in the first paragraph of Example 1, from 1.08 g of 1-isopropylamino-3-(4-hydroxyphenoxy)-2-propanol and 1.42 g of 2-[2-(4-chlorophenyl)ethoxy]ethyl methanesulfonate there were obtained 1.3 g (57%) of 1-[4-[2-(4-chlorophenethyloxy)-ethoxy]phenoxy]-3-isopropylamino-2-propanol hydrochloride of melting point 99°-101° C. (from ethyl acetate).

Sources & evidence

ORD record
ord-f3d96be446314547a8eb34ab89715121
Source dataset
uspto-grants-1987_03
Patent number
US04649160

Reaction notes

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