Potassium Carbonate → HCID 14989322, compound

HRID 981654Notes

Reaction equation

HRID 981654 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16]Cl)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[OH:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][O:18][C:19]3[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=3)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoateHCID 14989321HCID 14989321, compound

Product 1

HCID 14989322HCID 14989322, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4.1 parts of 3-choro-6-[4-(3-chloropropyl)-1-piperidinyl]pyridazine, 2.5 parts of ethyl 3-hydroxybenzoate, 14 parts of potassium carbonate and 94 parts of N,N-dimethylformamide was stirred overnight at 110° C. The reaction mixture was evaporated and the residue was taken up in water and dichloromethane. The separated organic layer was dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off, washed with 2-propanol and 2,2'-oxybispropane and dried at 50° C., yielding 4.6 parts (75.9%) of ethyl 3-[3-[1-(6-chloro-3-pyridazinyl)-4-piperidinyl]propoxy]benzoate; mp. 105.3° C. (comp. 99).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe separated organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was crystallized from 2-propanol
  6. filtrationThe product was filtered off
  7. washwashed with 2-propanol and 2,2'-oxybispropane
  8. customdried at 50° C.

Sources & evidence

ORD record
ord-6a737149572940b5a780195dc4887bc0
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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