Pyridine → HCID 12876713, compound

HRID 1701576Notes

Reaction equation

HRID 1701576 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[CH2:10][CH2:9][N:8]2[CH:17]=[O:18])=[CH:4][CH:3]=1.N1C=CC=CC=1.Br[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CCOCC.[Cu]>[O:1]([C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[CH2:10][CH2:9][N:8]2[CH:17]=[O:18])=[CH:19][CH:20]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 234600991-[(4-Hydroxyphenyl)methyl]-3,4,5,6,7,8-hexahydroisoquinoline-2(1H)-carbaldehyde

Product 1

HCID 12876713HCID 12876713, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 29.0 g (0.106 mol) of (±)-1-(p-hydroxybenzyl)-2-formyl-1,2,3,4,5,6,7,8-octahydroisoquinoline in 530 ml of freshly distilled pyridine was refluxed with stirring under nitrogen with 12.88 ml of bromobenzene, 51.5 g of copper (granular) and 22.55 g of potassium carbonate for 14 days. The reaction mixture after cooling was diluted with ether 1 l. and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in ether (300 ml). The ether solution was washed with 4 N aqueous sodium hydroxide (200 ml) then with water and dried. Removal of the solvent under reduced pressure gave 25.8 g (69%) of crude (±)-1-(p-phenoxybenzyl)-2-formyl-1,2,3,4,5,6,7,8-octahydroisoquinoline. For analysis, a sample of this compound was distilled, bp 220°-230° (0.05 mm Hq).

Workup

  1. temperatureThe reaction mixture after cooling
  2. filtrationand filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in ether (300 ml)
  5. washThe ether solution was washed with 4 N aqueous sodium hydroxide (200 ml)
  6. dry with materialwith water and dried
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-4b0352ecab6041988dfb7660df8354a9
Source dataset
uspto-grants-1980_03
Patent number
US04194044

Reaction notes

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