Trifluoroacetic acid → 1,2,3,4-Tetrahydro-8-isoquinolinecarbonitrile

HRID 991497Notes

Reaction equation

HRID 991497 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([C:18]#[N:19])[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:18]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH2:9][NH:8][CH2:17][CH2:16]2)#[N:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18414297HCID 18414297, compound

Product 1

HCID 184143391,2,3,4-Tetrahydro-8-isoquinolinecarbonitrileYield 105.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-t-butyloxycarbonyl-8-cyano-1,2,3,4-tetrahydroisoquinoline (1.4 g, 5.4 mmol) and trifluoroacetic acid (2 ml) in dichloromethane (20m1) was stirred at 40° C. for 16 h. Mixture was evaporated in vacuo and the resulting residue partitioned between dichloromethane and saturated potassium carbonate solution. The aqueous layer was extracted with more dichloromethane (2×100 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to afford the desired product as an amber oil (0.9 g, 100%).

Workup

  1. customMixture was evaporated in vacuo
  2. customthe resulting residue partitioned between dichloromethane and saturated potassium carbonate solution
  3. extractionThe aqueous layer was extracted with more dichloromethane (2×100 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9bd3f69b773649f99c3464b3f2c7c644
Source dataset
uspto-grants-2002_10
Patent number
US06465485B1

Reaction notes

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