Sodium Hydroxide → Benzyl 4-(piperidin-4-yl)piperazine-1-carboxylate

HRID 2265695Notes

Reaction equation

HRID 2265695 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[OH-].[Na+]>FC(F)(F)C(O)=O>[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:18][CH2:19]2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18971584Benzyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 57470863Benzyl 4-(piperidin-4-yl)piperazine-1-carboxylateYield 111.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To benzyl 4-(1-t-butoxycarbonylpiperidin-4-yl)piperazine 1-carboxylate (2.31 g) was added trifluoroacetic acid (10 ml) while cooling in an ice bath, followed by stirring at room temperature for 3 hr. The reaction mixture was poured into ice water, and a 5N aqueous solution of sodium hydroxide (26 ml) was added thereto. This was extracted with ethyl acetate:tetrahydrofuran=1:1. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed to provide the crude product of the titled compound as a pale yellow oil (1.93 g).

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionThis was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-ebd12f11d59442a59df8532c92243a10
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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