Sodium Carbonate → HCID 14989348, compound

HRID 1030937Notes

Reaction equation

HRID 1030937 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]Cl)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[OH:17][C:18]1[CH:30]=[CH:29][C:21]([C:22]([O:24][CH2:25][CH:26]2[CH2:28][CH2:27]2)=[O:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C(=O)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][O:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH:26]4[CH2:28][CH2:27]4)=[O:23])=[CH:29][CH:30]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 14989172HCID 14989172, compoundHCID 14989386HCID 14989386, compound

Product 1

HCID 14989348HCID 14989348, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2.6 parts of 3-chloro-6-[4-(2-chloroethyl)-1-piperidinyl]pyridazine, 1.9 parts of (cyclopropylmethyl) 4-hydroxybenzoate 1.1 parts of sodium carbonate and 94 parts of N,N-dimethylacetamide was stirred overnight at 110° C. After cooling, the reaction mixture was poured into water. The precipitated product was filtered off, washed with water and dissolved in trichloromethane. The organic layer was dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 2.9 parts (69.7%) of (cyclopropylmethyl) 4-[2-[1-(6-chloro-3-pyridazinyl)-4-piperidinyl]ethoxy]benzoate; mp. 134.0° C. (comp. 129).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitated product was filtered off
  3. washwashed with water
  4. dissolutiondissolved in trichloromethane
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from 2-propanol
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-c6b37ab65be44e2a812ed814df83e5bf
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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