Trifluoroacetic acid → 4-Chlorobenzylpiperazine

HRID 856095Notes

Reaction equation

HRID 856095 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 17723849Tert-butyl 4-(4-chlorobenzyl)piperazine-1-carboxylate

Product 1

HCID 1348264-ChlorobenzylpiperazineYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (8 ml) was added to a solution of tert-butyl 4-(4-chlorobenzyl)piperazine-1-carboxylate (2.50 g, 8.05 mmol) prepared in Reference Example 178 in methylene chloride (16 ml), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure. Sodium hydroxide aqueous solution was added to the residue, and the mixture was extracted with methylene chloride. The extract was dried over sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to afford 1-(4-chlorobenzyl)piperazine (1.70 g, quantitative) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionSodium hydroxide aqueous solution was added to the residue
  3. extractionthe mixture was extracted with methylene chloride
  4. dry with materialThe extract was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ea7c5460b94b4d55b8ce14d7b26541e5
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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