Hydrogen chloride-ethyl acetate → HCID 68935247, compound

HRID 1260926Notes

Reaction equation

HRID 1260926 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:14]([N:15]([CH3:24])[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:17])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.C(OCC)(=O)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:14]([N:15]([CH3:24])[C:16](=[O:17])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86631305rel-1,1-Dimethylethyl (3R,4R)-4-(benzoylmethylamino)-3-(3,4-dichlorophenyl)-1-piperidinecarboxylate

Product 1

HCID 68935247HCID 68935247, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound (0.455 g) obtained in Example 13 in ethyl acetate (3 mL) was added 4N hydrogen chloride/ethyl acetate solution (3 mL), and the mixture was stirred at room temperature for 24 hr with heating. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was made basic with 2N aqueous sodium hydroxide solution. The organic layer was separated, washed with water, and the solvent was evaporated under reduced pressure to give the title compound (0.27 g, 75%) as a white powder.

Workup

  1. temperaturewith heating
  2. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  3. additionwas added to the residue
  4. customThe organic layer was separated
  5. washwashed with water
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0349a66488aa48f59f90d58cab307f0c
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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