Trifluoroacetic acid → 7-{5-Chloro-2-[(2-pyridinylmethyl)oxy]phenyl}-1,2,3,4-tetrahydroisoquinoline

HRID 63291Notes

Reaction equation

HRID 63291 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][C:27]2[CH:32]=[C:31](C)[CH:30]=[CH:29][N:28]=2)=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15]3)=[CH:10][CH:9]=2)[CH:7]=1.C(O)(C(F)(F)F)=O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][NH:14][CH2:15]3)=[CH:10][CH:9]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 70664946HCID 70664946, compound

Product 1

HCID 706653527-{5-Chloro-2-[(2-pyridinylmethyl)oxy]phenyl}-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of, 1,1-dimethylethyl 7-(5-chloro-2-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate, (0.28 g) in DCM (1 ml) was added TFA (1 ml) and this was stirred at room temperature overnight. The reaction mixture was dissolved in water and backwashed with ethyl acetate. The aqueous layer was neutralised with aqueous sodium bicarbonate and extracted with ethyl acetate. The organics were dried over sodium sulphate and concentrated in vacuo to yield the title compound, 0.12 g

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organics were dried over sodium sulphate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ccba2ea0d9d942d7ab0a3ba174906e24
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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