2-(Benzylamino)ethan-1-ol--hydrogen chloride (1/1) → 1,2,3,4-Tetrahydroisoquinoline

HRID 1413940Notes

Reaction equation

HRID 1413940 reaction equation
Cl.O[CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.ClCCNCC1C=CC=CC=1>>[CH2:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:3][CH2:4][NH:5]1

Participants

3

Reactant 2

HCID 30171182-(Benzylamino)ethan-1-ol--hydrogen chloride (1/1)HCID 13054189Benzenemethanamine, N-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 70461,2,3,4-Tetrahydroisoquinoline

Procedure

The reactions of Examples 1 and 2 are repeated with equimolar quantities of N-hydroxyethylbenzylamine hydrochloride or N-chloroethylbenzylamine hydrochloride to give 1,2,3,4-tetrahydroisoquinoline. The use of N-chloroethyl-2,3-dichlorobenzylamine as the base gives good yields of 7,8-dichlorol,2,3,4-tetrahydroisoquinoline.

Sources & evidence

ORD record
ord-5843ca5528a94d8c8d21852df7d448a1
Source dataset
uspto-grants-1981_02
Patent number
US04251660

Reaction notes

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