Trifluoroacetic acid → 1-(Pyridin-4-yl)-4-(1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidine-4-carboxylic acid ethyl ester

HRID 412524Notes

Reaction equation

HRID 412524 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:19][C:20]3([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)[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>[CH2:35]([O:34][C:32]([C:20]1([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][N:23]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:22][CH2:21]1)=[O:33])[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 600641857-[4-Ethoxycarbonyl-1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 600641381-(Pyridin-4-yl)-4-(1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidine-4-carboxylic acid ethyl esterYield 95.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 7-[4-ethoxycarbonyl-1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester (10.87 g) in chloroform (50 ml) was dropwise added trifluoroacetic acid (30 ml) with ice-cooling, and the mixture was stirred at room temperature for 30 min. The solvent was evaporated and to the obtained residue was added aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was dried under reduced pressure to give the title compound (8.29 g).

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated and to the obtained residue
  3. additionwas added aqueous sodium hydrogencarbonate solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-2167c6508be6428e893d7279732128d3
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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