1-Naphthol → Propranolol

HRID 2198837Notes

Reaction equation

HRID 2198837 reaction equation
[CH:1]([N:4]1[CH2:7][CH:6]([OH:8])[CH2:5]1)([CH3:3])[CH3:2].[C:9]1([OH:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1>>[C:9]1([O:19][CH2:5][CH:6]([OH:8])[CH2:7][NH:4][CH:1]([CH3:2])[CH3:3])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 70051-NaphtholHCID 5446771-(Propan-2-yl)azetidin-3-ol

Product 1

HCID 4946Propranolol

Procedure

1-(isopropyl)-3-azetidinol and α-naphthol were reacted in the same manner as in Example 6 to form 1(-α-naphthoxy)-3-(iso-propylamino)-2-propanol. Then the propanol was dissolved in anhydrous ether and was converted to a hydrochloride by blowing a hydrochloric acid gas into the resulting solution. As a result, 1-(α-naphthoxy)-3-(iso-propylamino)-2-propanol hydrochloride melting at 162°-164° C. was obtained.

Sources & evidence

ORD record
ord-6e6349ee2cee42d489856d17ebc4f5d6
Source dataset
uspto-grants-1982_11
Patent number
US04360464

Reaction notes

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