Trifluoroacetic acid → 1-(3-Chlorobenzyl)piperazine

HRID 1783326

Reaction equation

HRID 1783326 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[Cl:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 4316940Tert-butyl 4-[(3-chlorophenyl)methyl]piperazine-1-carboxylate

Product 1

HCID 7647271-(3-Chlorobenzyl)piperazine

Procedure

To 4-(3-chlorobenzyl)-piperazine-1-carboxylic acid tert-butyl ester (20.24) (8.82 g, 28.4 mmol) is added TFA (45 mL) at ambient temperature over 5 min. After 1 h 50 min, TFA is evaporated, the residue is dissolved in 2N HCl (45 mL) and extracted with ether (2×45 mL). The aqueous layer is basified to pH 13 with 2N NaOH (60 mL) and extracted with CH2Cl2 (6×90 mL). The combined organic extracts are washed with brine (75 mL) and dried over MgSO4. The crude material obtained after filtration and concentration (5.44 g, 25.8 mmol, 91%) is used without further purification. MS (ES): m/z 211.0/213.0 (100/35) [MH+]. tR (method B)=5.1 min.

Workup

  1. customAfter 1 h 50 min, TFA is evaporated
  2. dissolutionthe residue is dissolved in 2N HCl (45 mL)
  3. extractionextracted with ether (2×45 mL)
  4. extractionextracted with CH2Cl2 (6×90 mL)
  5. washThe combined organic extracts are washed with brine (75 mL)
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-d33f0fe59b9f4c7fb9bb1a4030d09d4b
Source dataset
uspto-grants-2009_03
Patent number
US07501407B2

Linked notes

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