Sodium Bicarbonate → 3-Phenyl-2-(1,2,3,4-tetrahydroisoquinolin-7-yl)propanenitrile

HRID 2167442Notes

Reaction equation

HRID 2167442 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH:18]([C:26]#[N:27])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C([O-])(O)=O.[Na+]>C(O)=O>[C:20]1([CH2:19][CH:18]([C:12]2[CH:11]=[C:10]3[C:15]([CH2:16][CH2:17][NH:8][CH2:9]3)=[CH:14][CH:13]=2)[C:26]#[N:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 66978151tert-Butyl-7-(1-cyano-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 667475123-Phenyl-2-(1,2,3,4-tetrahydroisoquinolin-7-yl)propanenitrileYield 85.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

0.171 mmol tert-butyl-7-(1-cyano-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate were dissolved in 1.3 ml formic acid and stirred at room temperature for 1 h. After addition of saturated NaHCO3 solution the mixture was extracted with EtOAc. The combined organic layers were dried over MgSO4 and filtered. Evaporation of the solvent gave 38.5 mg of solid material (86%).

Workup

  1. extractionwas extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-182c55481b8640a6a295e1b419dd7cf6
Source dataset
uspto-grants-2015_06
Patent number
US09045459B2

Reaction notes

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