Dichloromethane → HCID 19898862, compound

HRID 1196523Notes

Reaction equation

HRID 1196523 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.[OH-].[K+].ClCCl>O>[C:10]1([C:8]2[CH:7]=[CH:6][N:5]=[C:4]([CH2:3][N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:9]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 31268PyrrolidineHCID 198988332-(Chloromethyl)-4-phenylpyridine--hydrogen chloride (1/1)

Product 1

HCID 19898862HCID 19898862, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The product from stage (i) (14.0 g) was added to a solution of pyrrolidine (17.0 ml) in water (80 ml) at 22°. The solution was stirred for 1 h at 22° and then potassium hydroxide (40 g), dichloromethane (200 ml) and water (200 ml) were added. The mixture was stirred for 0.25 h and the phases were separated. The aqueous phase was extracted with dichloromethane (100 ml) and the combined organic extracts were washed with water (2×100 ml), saturated brine, dried and evaporated to leave an oil (15.2 g), a portion of which (0.5 g) was purified by flash chromatography eluting with dichloromethane, ethanol and ammonia (200:8:1) to give the title compound as an oil (0.4 g). T.l.c. Silica (Dichloromethane, ethanol and ammonia 200:8:1) Rf 0.4.

Workup

  1. stirringThe mixture was stirred for 0.25 h
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with dichloromethane (100 ml)
  4. washthe combined organic extracts were washed with water (2×100 ml), saturated brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-42496f848be14efa9b08da8ec0996a26
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

Loading…