Hydrochloric Acid → HCID 22264624, compound

HRID 1267991Notes

Reaction equation

HRID 1267991 reaction equation
C(OC([NH:8][CH:9]([C:18]([N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:22][CH2:21]1)=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=O)(C)(C)C.C(Cl)Cl.FC(F)(F)C(O)=O.Cl>C(OCC)(=O)C.CCOCC>[NH2:8][CH:9]([C:18]([N:20]1[CH2:21][CH2:22][N:23]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:24][CH2:25]1)=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22264278HCID 22264278, compound

Product 1

HCID 22264624HCID 22264624, compoundYield 114.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(1-(t-butoxycarbonyl)amino-2-(4-chlorophenyl)ethyl)carbonyl-4-(benzyl)piperazine (0.20 g, 0.44 mmol) in a solution of CH2Cl2 (3 mL) was added trifluoroacetic acid (3 mL). The resultant mixture was stirred at ambient temperature. After 18 hours, the mixture was concentrated in vacuo to afford a yellow oil. This was dissolved in ethyl acetate and washed with an aqueous NaHCO3 solution. The organic layer was separated, dried over MgSO4, filtered and concentrated in vacuo to afford 0.17 g of a clear, colorless film. This was dissolved in ether and treated with an ethereal solution of HCl, resulting in formation of a white precipitate. Concentration afforded 0.18 g of 1-(1-amino-2-(4-chlorophenyl)ethyl)carbonyl-4-(benzyl)piperazine as a white solid; NMR (CDCl3) 7.4 (m, 7), 7.1 (m, 2), 4.0 (t, 1), 3.7-3.1 (m, 4), 2.8 (m, 2), 2.4-2.2 (m, 5), 1.8 (m, 1) ppm.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto afford a yellow oil
  3. washwashed with an aqueous NaHCO3 solution
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford 0.17 g of a clear, colorless film
  9. customresulting in formation of a white precipitate
  10. concentrationConcentration

Sources & evidence

ORD record
ord-b457575e6a8f4543aea17feb5a12e98b
Source dataset
uspto-grants-2003_04
Patent number
US06555537B2

Reaction notes

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