Water → 1-Adamantan-2-yl-4,4-dimethyl-imidazolidin-2-one

HRID 1092333Notes

Reaction equation

HRID 1092333 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][CH2:12][C:13]([CH3:16])([NH2:15])[CH3:14])[CH2:8]2.[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18].O>C1COCC1>[CH:3]12[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]([CH2:8]3)[CH:2]1[N:11]1[CH2:12][C:13]([CH3:16])([CH3:14])[NH:15][C:17]1=[O:18])[CH2:4]2

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 84088000N1-Adamantan-2-yl-2-methyl-propane-1,2-diamine

Product 1

HCID 249665551-Adamantan-2-yl-4,4-dimethyl-imidazolidin-2-oneYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N1-Adamantan-2-yl-2-methyl-propane-1,2-diamine (250 mg) was dissolved in dry THF (6 mL) under argon and carbonyldiimidazole (182 mg) was added. The resulting mixture was allowed to stir at RT for 48 hours. The mixture was poured into water/0.5 M HCl and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography using (a gradient of 10 to 70% ethyl acetate in heptane as an eluent. The fractions containing the desired material were combined and evaporated to leave 1-adamantan-2-yl-4,4-dimethyl-imidazolidin-2-one as a white solid (256 mg). MS (EI): 248.3 (M+).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography
  7. additionThe fractions containing the desired material
  8. customevaporated

Sources & evidence

ORD record
ord-f33478646b564644896c3c4460e00ff5
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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