Trifluoroacetic acid → HCID 68776969, compound

HRID 1711176Notes

Reaction equation

HRID 1711176 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][CH:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][OH:21])[CH2:14][CH2:13]1)[CH3:11])(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][CH:10]([N:12]1[CH2:13][CH2:14][CH:15]([NH:18][CH:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:20][OH:21])[CH2:16][CH2:17]1)[CH3:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 68774900HCID 68774900, compound

Product 1

HCID 68776969HCID 68776969, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The above carbamate (159 mg, 0.407 mmol) was dissolved in CH2Cl2 (4 ml) and then cooled to 0° C. Trifluoroacetic acid (2.0 ml, 26 mmol) was added dropwise to the cooled solution and then the reaction was allowed to stir for 10 minutes at 0° C., and then 30 minutes at room temperature. The solution was concentrated and the residue dissolved in 9:1 CH2Cl2/MeOH (10 ml). mgSO4 was added and the reaction mixture stirred for 30 minutes, then potassium carbonate (373 mg, 2.70 mmol) was added and the solution was concentrated to afford 2-[1-(3-amino-1-methylpropyl)piperidin-4-ylamino]-2-phenylethanol as a light yellow oil (106 mg, 89%) following purification.

Workup

  1. custom30 minutes
  2. customat room temperature
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue dissolved in 9:1 CH2Cl2/MeOH (10 ml)
  5. additionmgSO4 was added
  6. stirringthe reaction mixture stirred for 30 minutes
  7. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-a79fc0f714fa4a97ae9ea148673a30a6
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

Loading…