Trifluoroacetic acid → 1-[1-(1-Methylpiperidin-4-yl)-1-phenylethyl]piperazine

HRID 1992700Notes

Reaction equation

HRID 1992700 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([N:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[CH2:4][CH2:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([N:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59716946Tert-butyl 4-[1-(1-methylpiperidin-4-yl)-1-phenylethyl]piperazine-1-carboxylate

Product 1

HCID 597169471-[1-(1-Methylpiperidin-4-yl)-1-phenylethyl]piperazineYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[1-(1-methylpiperidin-4-yl)-1-phenylethyl]piperazine-1-carboxylate 0.16 g (0.41 mmol) in methylene chloride (20 ml) was added trifluoroacetic acid (5 ml) and resulting mixture stirred at room temperature for 2 hours. The reaction mixture was concentrated, dissolved in methylene chloride and washed with saturated sodium bicarbonate and brine. The methylene chloride solution was dried over sodium sulfate and concentrated to give 0.1 g (yield 82%) of desired product.

Workup

  1. customresulting mixture
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in methylene chloride
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialThe methylene chloride solution was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8ebf162d9b014f1d95615cf106528b4a
Source dataset
uspto-grants-2010_01
Patent number
US07649092B2

Reaction notes

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