Toluene → HCID 15718814, compound

HRID 2166134Notes

Reaction equation

HRID 2166134 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][C:15]3[N:23]([CH2:24][CH2:25][O:26][CH2:27][CH:28]=[CH2:29])[C:18]4=[N:19][CH:20]=[CH:21][CH:22]=[C:17]4[N:16]=3)[CH2:10][CH2:9]2)C=CC=CC=1.CC1C=CC=CC=1.[C:37](Cl)(=[O:41])[O:38][CH2:39][CH3:40].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:27]([O:26][CH2:25][CH2:24][N:23]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[N:16]=[C:15]1[CH2:14][CH:11]1[CH2:10][CH2:9][N:8]([C:37]([O:38][CH2:39][CH3:40])=[O:41])[CH2:13][CH2:12]1)[CH:28]=[CH2:29]

Participants

6

Reactant 4

HCID 1140TolueneHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 15718843HCID 15718843, compound

Product 1

HCID 15718814HCID 15718814, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and refluxed mixture of 13.5 parts of 2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-3-[2-(2-propenyloxy)ethyl)-3H-imidazo[4,5-b]-pyridine and 90 parts of methylbenzene were added dropwise 5.4 parts of ethyl carbonochloridate. Upon complete addition, stirring was continued for 1 hour at reflux temperature. After cooling, the reaction mixture was diluted with water and the whole was treated with potassium carbonate. The product was extracted with methylbenzene. The extract was dried, filtered and evaporated, yielding 14 parts (75.1%) of ethyl 4-[[3-[2-(2-propenyloxy)ethyl]-3H-imidazo[4,5-b]pyridine-2-yl]methyl]-1-piperidinecarboxylate as a residue (compound 43).

Workup

  1. temperaturerefluxed
  2. additionUpon complete addition
  3. stirringstirring
  4. temperatureat reflux temperature
  5. temperatureAfter cooling
  6. extractionThe product was extracted with methylbenzene
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-3bc6194a5a884e499519d8d266cab5c4
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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