Diketene → HCID 23004067, compound

HRID 396625Notes

Reaction equation

HRID 396625 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[NH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:23][CH3:24])=[C:16]([O:21][CH3:22])[CH:17]=2)[CH2:12]1>C1COCC1>[CH3:22][O:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:23][CH3:24])[CH2:12][N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6])[CH2:20][CH2:19]2

Participants

4

Reactant 2

HCID 12661DiketeneHCID 230040563,4-Dihydro-6,7-dimethoxy-2(1H)-isoquinolinepropanamine

Product 1

HCID 23004067HCID 23004067, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diketene (1.41 mL, 18.3 mmol, 1.50 equiv) was added at 0° C. to a stirred solution of 2-(3-aminopropyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline (3.05 g, 12.2 mmol, 1.00 equiv) in anhydrous THF (30 mL) under argon, and stirring was continued at room temperature for 1.5 hours. The mixture was concentrated and the residual oil washed with hexane (2×100 mL) to give 4.07 g (100%) of brown oil, which was characterized spectroscopically and used for the next reaction without purification.

Workup

  1. concentrationThe mixture was concentrated
  2. washthe residual oil washed with hexane (2×100 mL)

Sources & evidence

ORD record
ord-c4096cc82df548e383c6d5b082eaf76b
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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