1-Phenyl-1,2,3,4-tetrahydro-isoquinoline

Off-White Solid

General procedure: To a solution of alcohol 1 (1.0 mmol) in DMSO (2 mL), was added at 0 C propylphosphonic anhydride (T3P) (1.0 mmol, 50 % solution in ethyl acetate) and the resulting reaction mixture was stirred at room temperature for 1-2 h under nitrogen atmosphere. The reaction was monitored by TLC, after the completion of reaction, the solvent was removed under reduced pressure. The crude product was taken in toluene, amine 2 (1.2 mmol) and acetic acid (0.5 equiv) was added and stirred further for 1-2 h. After completion of the reaction, the mixture was diluted with water (20 mL) and neutralized with 10 % NaHCO3 solution. The product was extracted with ethyl acetate (10 mL) and the combined organic phase was washed with water (10 mL) and brine solution. The organic phase was dried over anhydrous Na2SO4. The solvent was dried under reduced pressure to afford a crude product, which was purified on silica gel using ethyl acetate and petroleum ether (Scheme-I).

1-Phenyl-1,2,3,4-tetrahydroisoquinoline is a Solifenacin (S676700) intermediate. 1-Phenyl-1,2,3,4-tetrahydroisoquinoline had been detected in parkinsonian human brain. 1-Phenyl-1,2,3,4-tetrahydroisoqu inoline maybe a candidate for endogenous MPTP-like neurotoxin since it is a structural analogue of MPTP which produces parkinsonism in humans.

Molecular Weight:209.29
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:209.120449483
Monoisotopic Mass:209.120449483
Topological Polar Surface Area:12
Heavy Atom Count:16
Complexity:220
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes