Hydrochloric Acid → 3-(4-Aminomethyl-phenyl)-1-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-1-isopropyl-urea

HRID 1057978Notes

Reaction equation

HRID 1057978 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:18]([CH2:22][CH:23]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[OH:24])[CH:19]([CH3:21])[CH3:20])=[O:17])=[CH:11][CH:10]=1)(C)(C)C.Cl>CCOC(C)=O>[NH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:17])[N:18]([CH2:22][CH:23]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[OH:24])[CH:19]([CH3:21])[CH3:20])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23560247(4-{3-[2-(3,4-Dichloro-phenyl)-2-hydroxy-ethyl]-3-isopropyl-ureido}-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 186725123-(4-Aminomethyl-phenyl)-1-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-1-isopropyl-ureaYield 92.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Through a solution of 3 g (6 mmol) (4-{3-[2-(3,4-Dichloro-phenyl)-2-hydroxy-ethyl]-3-isopropyl-ureido}-benzyl)-carbamic acid tert-butyl ester in 100 mL EtOAc was gently bubbled HCl gas for 15 min. The reaction mixture was then concentrated in vacuo and to the resulting residue was added 15 mL 1N LiOH solution. This was extracted 3×70 ml EtOAc and the combined extracts were washed with 10 ml brine, dried over Na2SO4, filtered and concentrated to give 2.2 g 3-(4-Aminomethyl-phenyl)-1-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-1-isopropyl-urea as a white solid which was used without further purification. 1H NMR(300 mHz, CD3OD) 7.71 (d, 1H, J=2 Hz); 7.53 (d, 1H, J=8 Hz); 7.37 (dd, 1H, J=8 and 2 Hz); 7.28 (m, 4H); 4.88(m, 1H); 4.34 (sept, 1H, J=7 Hz); 3.78 (s, 2H); 3.48(dd, 1H, J=9 and 16 Hz); 3.22 (m, 2H); 1.25 (d, 3H, J=7 Hz); 1.12 (d, 3H, J=7 Hz).

Workup

  1. customfor 15 min
  2. concentrationThe reaction mixture was then concentrated in vacuo and to the resulting residue
  3. additionwas added 15 mL 1N LiOH solution
  4. extractionThis was extracted 3×70 ml EtOAc
  5. washthe combined extracts were washed with 10 ml brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e412d0bb225248b69221b3ea0a523e4d
Source dataset
uspto-grants-2003_02
Patent number
US06515023B2

Reaction notes

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