Trifluoroacetic acid → HCID 11130484, compound

HRID 2104320Notes

Reaction equation

HRID 2104320 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([C@H:16]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][N:26]([CH3:28])[CH3:27])[CH2:21][CH2:20]1)=[O:18])C)(C)(C)C>ClCCl>[CH3:27][N:26]([CH2:25][CH:22]1[CH2:23][CH2:24][N:19]([C:17](=[O:18])[C@H:16]([NH:14][CH3:13])[CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:20][CH2:21]1)[CH3:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11825613HCID 11825613, compound

Product 1

HCID 11130484HCID 11130484, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., trifluoroacetic acid (20 ml) was added to a solution of N-[(1R)-1-benzyl-2-(4-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester (1.22 g, 3.02 mmol) in dichloromethane (20 ml). The reaction mixture was stirred for 1 h at 0° C. The solvents were removed in vacuo. The residue was dissolved in dichloromethane (70 ml) and the solvent was removed in vacuo. The latter procedure was repeated two times. The crude product was purified by flash chromatography on silica (100 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1), to give 659 mg of (2R)-1-(4-((dimethylamino)methyl)piperidin-1-yl)-2-(methylamino)-3-phenylpropan-1-one.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (70 ml)
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by flash chromatography on silica (100 g)

Sources & evidence

ORD record
ord-5efd820ca785433db56a8407609ddbdc
Source dataset
uspto-grants-2009_08
Patent number
US07576062B2

Reaction notes

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