Trifluoroacetic acid → 1-(1-Benzylpiperidin-3-yl)piperazine

HRID 499225Notes

Reaction equation

HRID 499225 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:22]2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH2:27]([N:23]1[CH2:24][CH2:25][CH2:26][CH:21]([N:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)[CH2:22]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 684554544-(1-Benzylpiperidin-3-yl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 178125061-(1-Benzylpiperidin-3-yl)piperazineYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

30 g of TFA are added to a solution of 9.2 g of the compound obtained in step 4.1, in 85 ml of DCM. The medium is stirred at AT for 5 h, and then concentrated. The crude obtained is taken up in DCM and then washed 4 times with a 2M sodium hydroxide solution. The organic phase is washed with a saturated NaCl solution. After drying over MgSO4, the organic phase is concentrated, to give 6.32 g of the expected product.

Workup

  1. concentrationconcentrated
  2. customThe crude obtained
  3. washwashed 4 times with a 2M sodium hydroxide solution
  4. washThe organic phase is washed with a saturated NaCl solution
  5. dry with materialAfter drying over MgSO4
  6. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-9355e5f415604fb4a0b171ad2422ac80
Source dataset
uspto-grants-2010_08
Patent number
US07767681B2

Reaction notes

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