Trifluoroacetic acid → HCID 18713602, compound

HRID 228118Notes

Reaction equation

HRID 228118 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1)[CH3:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21935152HCID 21935152, compound

Product 1

HCID 18713602HCID 18713602, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-{2-[(dimethylamino)methyl]phenyl}-piperazine carboxylate (Step 2) (0.68 g, 2.1 mmol) dissolved in CH2Cl2 (12 mL) was added TFA (6 mL). After stirring the reaction at RT for 1 h, the solvent was concentrated in vacuo and the residue was partitioned between CH2Cl2 and satd NaHCO3. The organic layer was washed with brine and the combined aqueous layer were extracted with a mixture of CH2Cl2 and 30% MeOH. The combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give dimethyl[(2-piperazinylphenyl)methyl]amine as a yellow oil (0.35 g). MS m/z: 220 (M+H). Calc'd for C13H21N3: 219.33.

Workup

  1. customthe reaction at RT for 1 h
  2. concentrationthe solvent was concentrated in vacuo
  3. customthe residue was partitioned between CH2Cl2
  4. washThe organic layer was washed with brine
  5. extractionthe combined aqueous layer were extracted with a mixture of CH2Cl2 and 30% MeOH
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2f885c104a34d6c9b0d5b8842aeddd4
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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