Acetic Acid → (+)-(R)-N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamide

HRID 714050Notes

Reaction equation

HRID 714050 reaction equation
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C@@H:7]([NH2:12])[C:6]=2[CH:5]=[N:4][CH:3]=1.[C:13](O)(=[O:15])[CH3:14]>>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C@@H:7]([NH:12][C:13](=[O:15])[CH3:14])[C:6]=2[CH:5]=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 86679930(R)-4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-amine

Product 1

HCID 86699310(+)-(R)-N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamideYield 91%

Procedure

In analogy to the procedure described for the preparation of intermediate A-4 [D], (+)-(R)-4-bromo-5,6,7,8-tetrahydroisoquinolin-8-amine (intermediate A-11) and acetic acid gave the title compound as off-white solid in 91% yield. MS: 269.0 (M+H+, 1Br).

Sources & evidence

ORD record
ord-659cfb1312ff426a8c0b46be316416db
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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