Trimethyl methanetricarboxylate → HCID 71284187, compound

HRID 1481696Notes

Reaction equation

HRID 1481696 reaction equation
CC([N:5]=[C:6]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH:14]=[CH:13]2)[CH2:7][CH2:8][CH3:9])(C)C.[CH:20]([C:29]([O:31][CH3:32])=[O:30])([C:25](OC)=[O:26])[C:21](OC)=[O:22]>O(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:8]([C:7]1[C:21]([OH:22])=[C:20]([C:29]([O:31][CH3:32])=[O:30])[C:25](=[O:26])[NH:5][C:6]=1[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH:14]=[CH:13]2)[CH3:9]

Participants

4

Reactant 2

HCID 136922Trimethyl methanetricarboxylateHCID 89422873HCID 89422873, compound

Product 1

HCID 71284187HCID 71284187, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
230 °C

Procedure

To a suspension of 2-methyl-N-(1-(1-methyl-1H-indol-5-yl)butylidene)propan-2-amine (6.70 g, ca. 26.1 mmol), prepared according to procedure described in Example 21 Step 2, in Ph2O (40 mL) was added trimethyl methanetricarboxylate (8.44 g, 44.4 mmol, 1.7 eq). Distillation apparatus was set up then attached to the flask. The reaction was stirred at 230° C. for 10 min then heating was removed. The mixture was cooled to room temperature. The precipitate was collected by filtration then washed with diethyl ether to afford the title compound as a yellow solid (4.85 g, 14.9 mmol, 55%).

Workup

  1. customprepared
  2. distillationDistillation apparatus
  3. temperaturethen heating
  4. customwas removed
  5. temperatureThe mixture was cooled to room temperature
  6. filtrationThe precipitate was collected by filtration
  7. washthen washed with diethyl ether

Sources & evidence

ORD record
ord-c5a56667411842c8af4675e3f379aa45
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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