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

HRID 382684Notes

Reaction equation

HRID 382684 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 The residue
  4. customwas 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-44e614fb4c034006a5d7276faa2fabb9
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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