1,2,3,4-Tetrahydroisoquinoline → N-[3-(1,2,3,4-Tetrahydroisoquinolin-2-yl)propyl]acetoacetamide

HRID 396627Notes

Reaction equation

HRID 396627 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:11])[CH2:7][C:8]([CH3:10])=[O:9].[CH2:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][NH:13]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][N:13]1[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:11])[CH2:7][C:8]([CH3:10])=[O:9]

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 23004079N-(3-bromopropyl)acetoacetamide

Product 1

HCID 23004192N-[3-(1,2,3,4-Tetrahydroisoquinolin-2-yl)propyl]acetoacetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of N-(3-bromopropyl)acetoacetamide (4.50 g, 20.3 mmol, 1.00 equiv), 1,2,3,4-tetrahydroisoquinoline (3.30 mL, 26.3 mmol, 1.30 equiv), K2CO3 (3.64 g, 26.3 mmol, 1.30 equiv), and KI (330 mg, 1.99 mmol, 0.10 equiv) in acetone (60 mL) was stirred at reflux for 14 hours. The mixture was cooled to room temperature, filtered, and concentrated. The residue was purified by flash chromatography (SiO2, MeOH-EtOAc 0:1 to 1:9) to give 1.78 g (43%) of light yellow oil, which was characterized spectroscopically. N-(3-Bromopropyl)acetoacetamide (1.20 g) was also recovered.

Workup

  1. temperatureat reflux for 14 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (SiO2, MeOH-EtOAc 0:1 to 1:9)
  5. customto give 1.78 g (43%) of light yellow oil, which
  6. customN-(3-Bromopropyl)acetoacetamide (1.20 g) was also recovered

Sources & evidence

ORD record
ord-673e563e2f254d5bac5cba5e54407083
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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