Water → HCID 59707065, compound

HRID 221954Notes

Reaction equation

HRID 221954 reaction equation
[C:1]([C:5]1[CH:35]=[CH:34][C:8]([CH2:9][N:10]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4C(=O)C5C(=CC=CC=5)C4=O)=[CH:18][CH:17]=3)[C:11]2=[O:33])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O>CO>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:12]2[CH2:13][CH2:14][N:10]([CH2:9][C:8]3[CH:34]=[CH:35][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][CH:7]=3)[C:11]2=[O:33])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 962WaterHCID 59707063HCID 59707063, compound

Product 1

HCID 59707065HCID 59707065, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-{4-[3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-ylmethyl]phenyl}isoindol-1,3-dione (E) (654 mg, 1.4 mmol) in MeOH (30 mL) hydrazine hydrate was added as a 0.8 M solution in MeOH (10 mL, 8 mmol) with stirring at RT. The reaction mixture was stirred for 90 min at RT and then H2O (50 mL) was added. The solvent was removed in vacuo and the residue was extracted with EtOAc (3×20 mL). The combined organic phases were dried over Na2SO4 and the solvent again removed in vacuo. There were obtained 430 g (91% of theory) of the desired product 1-(4-aminobenzyl)-3-(4-tert-butylbenzyl)-imidazolidin-2-one (F).

Workup

  1. stirringThe reaction mixture was stirred for 90 min at RT
  2. customThe solvent was removed in vacuo
  3. extractionthe residue was extracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customthe solvent again removed in vacuo

Sources & evidence

ORD record
ord-be8e1246273a467d95fd946ea401e0d0
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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