Trifluoroacetic acid → 2-Amino-1-[4-(3,4-dichlorophenoxy)-piperidine-1-yl]-3-methyl-butan-1-one

HRID 1059021Notes

Reaction equation

HRID 1059021 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([CH:14]([NH:18]C(=O)C)[CH:15]([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.FC(F)(F)C(O)=O>ClCCl>[NH2:18][CH:14]([CH:15]([CH3:17])[CH3:16])[C:12]([N:9]1[CH2:10][CH2:11][CH:6]([O:5][C:4]2[CH:22]=[CH:23][C:24]([Cl:25])=[C:2]([Cl:1])[CH:3]=2)[CH2:7][CH2:8]1)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22322354N-{1-{4-(3,4-Dichlorophenoxy)-piperidine-1-carbonyl]-2-methyl-propyl}-acetamide

Product 1

HCID 223224522-Amino-1-[4-(3,4-dichlorophenoxy)-piperidine-1-yl]-3-methyl-butan-1-oneYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step (i) (1.57 g) was dissolved in dichloromethane (14 ml) and trifluoroacetic acid (4 ml) added. After 2 hours at room temperature the solvent was removed, ethyl acetate and 2N aqueous NaOH solution were added to give pH 8.0. The organic phase was separated and concentrated to give the sub-titled product as an oil (1.24 g) which was used in the next step without further purification.

Workup

  1. customAfter 2 hours at room temperature the solvent was removed
  2. additionethyl acetate and 2N aqueous NaOH solution were added
  3. customto give pH 8.0
  4. customThe organic phase was separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-61ff540ec253445e99564861b9f1adb1
Source dataset
uspto-grants-2003_02
Patent number
US06518286B1

Reaction notes

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