HCID 67388622, compound → 1-Piperazinecarboxylic acid, 4-(4-piperidinylmethyl)-, 1,1-dimethylethyl ester

HRID 908455Notes

Reaction equation

HRID 908455 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][N:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C>[NH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][N:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]2)[CH2:13][CH2:12]1

Participants

3

Reactant 1

HCID 67388622HCID 67388622, compound

Product 1

HCID 673884751-Piperazinecarboxylic acid, 4-(4-piperidinylmethyl)-, 1,1-dimethylethyl esterYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of benzyl 4-formylpiperidine-1-carboxylate (3 g) and tert-butyl piperazine-1-carboxylate (2.2 g) in dichloromethane (100 ml) was added sodium triacetoxyborohydride ((2.6 g). The resulting solution was stirred at room temperature for 18 hours and then washed with 2M sodium hydroxide (2×50 ml) and 2M hydrochloric acid (2×50 ml), dried over Magnesium sulphate, filtered and evaporated to afford tert-butyl 4-[(1-benzyloxycarbonyl-4-piperidyl)methyl]piperazine-1-carboxylate (4.9 g) as an oil. Tert-butyl 4-[(1-benzyloxycarbonyl-4-piperidyl)methyl]piperazine-1-carboxylate (4.9 g) was dissolved in ethanol and purged with argon. 20% Palladium hydroxide on carbon (500 mg) was added. The reaction mixture was purged with argon, evacuated and filled with hydrogen from a balloon. The reaction mixture was stirred at room temperature for 2 hours. A white solid precipitate formed. The reaction mixture was warmed to 40° C. and stirred at this temperature for a further 1 hour until the precipitate dissolved. The reaction mixture was allowed to cool to room temperature and stirred for a further 18 hours. The reaction mixture was purged with argon, filtered through celite and evaporated to afford tert-butyl 4-(4-piperidylmethyl)piperazine-1-carboxylate (3.2 g) as a solid. Mass spectrum: M+H+ 284

Workup

  1. custompurged with argon
  2. addition20% Palladium hydroxide on carbon (500 mg) was added
  3. customThe reaction mixture was purged with argon
  4. customevacuated
  5. additionfilled with hydrogen from a balloon
  6. customA white solid precipitate formed
  7. temperatureThe reaction mixture was warmed to 40° C.
  8. stirringstirred at this temperature for a further 1 hour until the precipitate
  9. dissolutiondissolved
  10. temperatureto cool to room temperature
  11. stirringstirred for a further 18 hours
  12. customThe reaction mixture was purged with argon
  13. filtrationfiltered through celite
  14. customevaporated

Sources & evidence

ORD record
ord-979661edc62f46f6abf50ce7756b2df5
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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