Trifluoroacetic acid → 1-(4-Diisopropylaminomethylbenzoyl)piperazine

HRID 278549Notes

Reaction equation

HRID 278549 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(OCC)(=O)C>[CH:23]([N:22]([CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:29])=[CH:16][CH:17]=1)[CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 226280611-(Tert-butoxycarbonyl)-4-(4-diisopropylaminomethylbenzoyl)piperazine

Product 1

HCID 226279521-(4-Diisopropylaminomethylbenzoyl)piperazineYield 90.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-(4-diisopropylaminomethylbenzoyl)piperazine (4.6 g) in ethyl acetate (10 ml) was added trifluoroacetic acid (20 ml), and the solution was stirred at room temperature for 1 hour and concentrated. The residue was dissolved in water. The solution was made alkaline with sodium hydroxide solution, extracted with dichloromethane. The extract was dried and concentrated to give amorphous powders which were filtered, washed with hexane and dried to afford the title compound (3.12 g).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with dichloromethane
  4. customThe extract was dried
  5. concentrationconcentrated
  6. customto give amorphous powders which
  7. filtrationwere filtered
  8. washwashed with hexane
  9. customdried

Sources & evidence

ORD record
ord-084ef76c38a54aa4b696a7f2a3824efa
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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