Trifluoroacetic acid → 4-[4-(1,2,3,4-Tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridine-3-carboxylic acid methyl ester

HRID 412577Notes

Reaction equation

HRID 412577 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:19][CH:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][C:27]=4[C:32]([O:34][CH3:35])=[O:33])[CH2:22][CH2:21]3)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:35][O:34][C:32]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:26]=1[N:23]1[CH2:22][CH2:21][CH:20]([CH2:19][O: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)[CH2:25][CH2:24]1)=[O:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 112024757-[1-(3-Methoxycarbonylpyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 600641694-[4-(1,2,3,4-Tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridine-3-carboxylic acid methyl esterYield 102.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 7-[1-(3-methoxycarbonylpyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester (37 mg) in chloroform (0.5 ml) was added trifluoroacetic acid (0.15 ml), and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was evaporated. To the obtained residue was added aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and dried under reduced pressure to give the title compound (30 mg).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionTo the obtained residue was added aqueous sodium hydrogencarbonate solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-5b905cec32e34afcb56c70b183bfdad1
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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