Triethylamine → 4-[4-(3-Chloro-phenyl)-4-methyl-2-oxo-imidazolidin-1-yl] adamantane-1-carboxylic acid methyl ester

HRID 1092362Notes

Reaction equation

HRID 1092362 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH:8]3[NH:15][CH2:16][C:17]([NH2:26])([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[CH3:18])[CH2:6]1)[CH2:12]2)=[O:4].Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH:8]3[N:15]3[CH2:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)([CH3:18])[NH:26][C:28]3=[O:30])[CH2:6]1)[CH2:12]2)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 574956404-[2-Amino-2-(3-chloro-phenyl)-propylamino]-adamantane-1-carboxylic acid methyl ester

Product 1

HCID 249683544-[4-(3-Chloro-phenyl)-4-methyl-2-oxo-imidazolidin-1-yl] adamantane-1-carboxylic acid methyl esterYield 118.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-[2-amino-2-(3-chloro-phenyl)-propylamino]-adamantane-1-carboxylic acid methyl ester (7.9 g) in 40 mL DCM was cooled to −20° C. and triphosgene (3.1 g) (separately dissolved in 10 mL DCM) was added to it drop wise followed by drop wise addition of triethylamine (6.57 mL). The reaction mixture was slowly brought to RT and left at stirring for 4 h. Reaction was monitored by TLC. After completion, the reaction mixture was quenched with water and the DCM layer was separated. The aqueous layer was again extracted with DCM (2×). The combined DCM layers were dried over Na2SO4 and concentrated to afford the crude product, which was purified by column chromatography to give the desired 4-[4-(3-chloro-phenyl)-4-methyl-2-oxo-imidazolidin-1-yl] adamantane-1-carboxylic acid methyl ester (5.0 g) as a mixture of E/Z isomers as a white solid. MS (ES+): 403.4 (MH+).

Workup

  1. additionwas added to it drop
  2. customwas slowly brought to RT
  3. waitleft
  4. customReaction
  5. customAfter completion, the reaction mixture was quenched with water
  6. customthe DCM layer was separated
  7. extractionThe aqueous layer was again extracted with DCM (2×)
  8. dry with materialThe combined DCM layers were dried over Na2SO4
  9. concentrationconcentrated
  10. customto afford the crude product, which
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-da45119eb33e49c7a72678aff66902a3
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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