2-(((2,3-Dichlorophenyl)methyl)amino)ethanol hydrochloride → 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reaction equation

Cl.O[CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[Cl:14].[Cl-].[Al+3].[Cl-].[Cl-]>>[ClH:13].[Cl:13][C:9]1[C:8]([Cl:14])=[C:7]2[C:12]([CH2:3][CH2:4][NH:5][CH2:6]2)=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 30185402-(((2,3-Dichlorophenyl)methyl)amino)ethanol hydrochloride

HCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 1239197,8-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 174.2%

Procedure

A mixture of 2.0 g (7.8 mm) of N-hydroxyethyl-2,3-dichlorobenzylamine hydrochloride and 5 g (37.5 mm) of aluminum chloride was reacted as above with the aluminum chloride additions at 0 time, 2 g; 1/2 hour, 1 g and 11/4 hour, 2 g to give 1.62 g (87.1%) of 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride which is 97.93% pure by gas liquid chromatography.

Sources & evidence

ORD record: ord-47d8dfb1616b4bbc95d5b3ff24dc8da8
Source dataset: uspto-grants-1981_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04251660

Reaction notes

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