1,2,3,4-Tetrahydroisoquinoline → HCID 86729224, compound

HRID 1051437Notes

Reaction equation

HRID 1051437 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].[CH2:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][NH:15]1>CCO>[CH2:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][N:15]1[CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 27740493-(oxiran-2-ylmethoxy)benzaldehyde

Product 1

HCID 86729224HCID 86729224, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(oxiran-2-ylmethoxy)benzaldehyde (1.0 g, 5.61 mmol) and 1,2,3,4-tetrahydroisoquinoline (1.49 g, 11.22 mmol) in EtOH (20 mL) was heated at 110° C. for 3 h. The solvent was then removed by concentration and the residue dissolved in ethyl acetate, washed with water and the separated organic layer dried and concentrated. The crude product was purified by column chromatography. (1.1 g, yield 63%.) MS (ESI) e/z: 312.3 [M+1]+.

Workup

  1. customThe solvent was then removed by concentration
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water
  4. customthe separated organic layer dried
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6c95555f1f3c4175ab73ab721322ca69
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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