Water → N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

HRID 530342Notes

Reaction equation

HRID 530342 reaction equation
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([NH2:12])[C:6]=2[CH:5]=[N:4][CH:3]=1.CCN(CC)CC.[C:20](Cl)(=[O:23])[CH2:21][CH3:22].O>C(Cl)Cl>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([NH:12][C:20](=[O:23])[CH2:21][CH3:22])[C:6]=2[CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 717433794-Bromo-5,6,7,8-tetrahydroisoquinolin-8-amine

Product 1

HCID 86685953N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (rac)-4-bromo-5,6,7,8-tetrahydro-isoquinolin-8-ylamine (intermediate A-2 [D]) (3.7 g, 16.3 mmol) and Et3N (3.3 g, 32.6 mmol) in DCM (50 mL) was added propionyl chloride (2.25 g, 24.4 mmol) at 0° C. The resulting reaction mixture was stirred for 3 hr before it was warmed up to room temperature and poured into water (50 mL) and extracted with DCM (2×50 mL). The combined organic layers were then dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography and afforded the title compound (4.29 g, 93% yield) as a white solid. MS: 283.0 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with DCM (2×50 mL)
  3. customThe combined organic layers were then dried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7bab575ed6c643dd9eeeca2ac76da0ae
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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