Ammonium formate → 1-(Pyrimidin-4-yl)-4-(1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidine-4-carboxylic acid ethyl ester

HRID 412537Notes

Reaction equation

HRID 412537 reaction equation
C(OC([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][C:23]3([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31](Cl)[N:30]=4)[CH2:25][CH2:24]3)=[CH:16][CH:17]=2)[CH2:12]1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[C].[Pd]>[CH2:39]([O:38][C:36]([C:23]1([CH2:22][O:21][C:15]2[CH:14]=[C:13]3[C:18]([CH2:19][CH2:20][NH:11][CH2:12]3)=[CH:17][CH:16]=2)[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][N:30]=2)[CH2:25][CH2:24]1)=[O:37])[CH3:40]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 114104597-[1-(2-Chloropyrimidin-4-yl)-4-ethoxycarbonylpiperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester

Product 1

HCID 600641441-(Pyrimidin-4-yl)-4-(1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidine-4-carboxylic acid ethyl esterYield 146.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7-[1-(2-chloropyrimidin-4-yl)-4-ethoxycarbonylpiperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester (263 mg) in ethanol(5 ml) were added 7.5% palladium carbon (120 mg) and ammonium formate (200 mg) with ice-cooling, and the mixture was stirred under reflux for 30 min. After completion of the reaction, the solvent was evaporated and water was added to the obtained residue. The mixture was extracted with chloroform and the organic layer was washed with aqueous sodium hydrogencarbonate solution and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was dried under reduced pressure to give the title compound (270 mg).

Workup

  1. temperaturecooling
  2. temperatureunder reflux for 30 min
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated
  5. additionwater was added to the obtained residue
  6. extractionThe mixture was extracted with chloroform
  7. washthe organic layer was washed with aqueous sodium hydrogencarbonate solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated
  10. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-0cdff6e4f60d46478f28e1fc8817b0e5
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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