Oxygen → 1-cyano-N-phenyl-1,2,3,4-tetrahydroisoquinoline

HRID 1019326Notes

Reaction equation

HRID 1019326 reaction equation
[C:1]1([N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:17]#[N:18].[Na+].O=O.C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[C:17]([CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:16][N:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)#[N:18]

Participants

6

Reactant 4

HCID 977Oxygen3×HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 11321753HCID 11321753, compound

Product 1

HCID 112877551-cyano-N-phenyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Conditions

Temperature
60 °C

Procedure

N-phenyl-1,2,3,4-tetrahydroisoquinoline (1 mmol), RuCl3-nH2O (0.05 mmol) and sodium cyanide (1.2 mmol) were charged into a 25-ml side-arm flask, the interior of the reacting container was replaced by oxygen, and an oxygen balloon was attached to supply oxygen at 1 atm. Then, 1.7 ml of a mixed solvent of methanol-acetic acid (volume ratio 3/1) was added thereto at room temperature. Reaction was effected by stirring the mixed liquid at 60° C. for 4 hours. After the reaction mixture liquid was made alkaline with the addition of saturated sodium bicarbonate aqueous solution, the mixture was extracted with 10 ml ethyl acetate once and with 5 ml ethyl acetate twice. The extracted liquid thus obtained was washed with saturated saline solution, and dried over sodium sulfate, thereby obtaining an ethyl acetate solution of 1-cyano-N-phenyl-1,2,3,4-tetrahydroisoquinoline. After this solution was concentrated under reduced pressure, the mixture was analyzed by a 1H NMR internal standard method, which revealed the conversion rate of N-phenyl-1,2,3,4-tetrahydroisoquinoline being 91% with a yield of 1-cyano-N-phenyl-1,2,3,4-tetrahydroisoquinoline being 79% (vs. N-phenyl-1,2,3,4-tetrahydroisoquinoline). By using silica gel chromatography, 1-cyano-N-phenyl-1,2,3,4-tetrahydroisoquinoline was isolated at a yield of 76%.

Workup

  1. customat room temperature
  2. customReaction
  3. extractionthe mixture was extracted with 10 ml ethyl acetate once
  4. customThe extracted liquid thus obtained
  5. washwas washed with saturated saline solution
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-429f386ad67e462b8ebd43df77aa8422
Source dataset
uspto-grants-2002_11
Patent number
US06486340B2

Reaction notes

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