Water → L 646462

HRID 1248162Notes

Reaction equation

HRID 1248162 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:22]=[CH:23][CH:24]=[CH:25][C:9]2=3)[CH2:4][CH2:3]1.[CH2:26]([N:28]([CH2:31]C)CC)C.CN(C)P([N:40]([CH3:42])[CH3:41])(N(C)C)=O.[C:44](=[O:47])([O-])[O-].[Na+].[Na+].[OH2:50]>>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([C:19]([O:21][CH2:26][N:28]4[C:31](=[O:50])[CH2:42][N:40]([CH3:41])[C:44]4=[O:47])=[O:20])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:22]=[CH:23][CH:24]=[CH:25][C:9]2=3)[CH2:4][CH2:3]1

Participants

6

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 12679HexamethylphosphoramideHCID 12909376HCID 12909376, compound

Product 1

HCID 145990L 646462

Conditions

Temperature
100 °C

Procedure

To a mixture of 1.0 g (0.00302 mole) of (±)-5-(1-methyl-4-piperidylidene)-5H-dibenzo[a,d]-cycloheptene-3-carboxylic acid, 0.31 g (0.0030 mole) of triethylamine and 4 ml of hexamethylphosphoramide was added 0.456 g (0.0030 mol) of 1H-1-chloromethyl-3-methyl-2,5-dioxo-2,3,4,5-tetrahydroimidazole. The mixture was stirred and heated in an oil bath at 100° C. for 18 hours. After cooling, 25 ml of water and 25 ml of a saturated solution of sodium carbonate were added to the reaction. The mixture then was extracted with ten 50 ml aliquots of ether. The combined ether extracts were washed with ten 75 ml portions of water, dried over magnesium sulfate, filtered, and the solvent was removed on a rotary evaporator. The white crystalline residue was recrystallized from acetonitrile to afford (±)-(3-methyl-2,5-dioxo-1-imidazolidinyl)methyl 5-(1-methyl-4-piperidinylidene)-5H-dibenzo[a,d]cycloheptene-3-carboxylate, m.p. 192°-194°.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture then was extracted with ten 50 ml aliquots of ether
  3. washThe combined ether extracts were washed with ten 75 ml portions of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed on a rotary evaporator
  7. customThe white crystalline residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-77b364262c664c08a58dbb23152c33c1
Source dataset
uspto-grants-1985_06
Patent number
US04522821

Reaction notes

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