Pyridine → HCID 12876713, compound

HRID 2287250Notes

Reaction equation

HRID 2287250 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 1. and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in ether (300 ml). The ether solution was washed with 4N 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 4N 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-f7cb005669c24e3ca2d8db8fe05cdfaa
Source dataset
uspto-grants-1981_05
Patent number
US04270000

Reaction notes

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