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

HRID 1399804Notes

Reaction equation

HRID 1399804 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-63c3467fdb3f4ca0929324ac1136a1dd
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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