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

HRID 880011Notes

Reaction equation

HRID 880011 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-be5d669b50eb4796aee56e3ab999f139
Source dataset
uspto-grants-2015_03
Patent number
US08993560B2

Reaction notes

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