Dimethylamine → HCID 15411270, compound

HRID 2293294Notes

Reaction equation

HRID 2293294 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][N:3]=1.[CH3:24][NH:25][CH3:26]>C(O)C>[CH3:24][N:25]([CH3:26])[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 15411267HCID 15411267, compound

Product 1

HCID 15411270HCID 15411270, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

4.5 g of 2-chloro-5-[(cyclopentylidene)(4-methylsulfonylphenyl)-methyl]pyridine, prepared in Example 6, and 50 ml of a 33% solution of dimethyl-amine in ethanol are placed in a 125 ml autoclave. The mixture is heated at 180° C. under pressure for 7 hours. After cooling, the solvent is evaporated off under vacuum and the residue is taken up with water and then extracted with dichloromethane. The organic phase is dried over magnesium sulfate and evaporated under vacuum. The resulting oil crystallizes from an ethyl ether/isopropyl ether mixture to give 2.8 g of 2-(dimethylamino)-5-[(cyclopentylidene)(4-methylsulfonylphenyl)methyl]pyridine in the form of crystals melting at 122°-123° C.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated off under vacuum
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customevaporated under vacuum
  6. customThe resulting oil crystallizes from an ethyl ether/isopropyl ether mixture

Sources & evidence

ORD record
ord-59b1510727b9411f93954494c6eaa723
Source dataset
uspto-grants-1997_11
Patent number
US05686460

Reaction notes

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