Propionic Acid → (R)-N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

HRID 714058Notes

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:16])[CH2:14][CH3:15]>>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C@@H:7]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[C:6]=2[CH:5]=[N:4][CH:3]=1

Participants

Reactant 2

HCID 1032Propionic Acid

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

Product 1

HCID 86699312(R)-N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamideYield 97%

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 propionic acid gave the title compound as white solid in 97% yield. MS: 283.5 (M+H+, 1 Br).

Sources & evidence

ORD record: ord-6b49f2d022e1499ebe215551943a201b
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187429B2

Reaction notes

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