Water → HCID 20542601, compound

HRID 2285912Notes

Reaction equation

HRID 2285912 reaction equation
[C:1]1([C:7]2([OH:20])[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:24]1[CH:29]=[N:28][CH:27]=[CH:26][N:25]=1.O>CS(C)=O>[C:1]1([C:7]2([O:20][C:24]3[CH:29]=[N:28][CH:27]=[CH:26][N:25]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 73277ChloropyrazineHCID 973334-Piperidinol, 1-benzyl-4-phenyl-

Product 1

HCID 20542601HCID 20542601, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-phenyl-1-phenylmethyl-4-piperidinol (5.35 g, 20 mM) in DMSO (50 ml) was treated with sodium hydride (960 mg of a 50% dispersion, 20 mM) followed by chloropyrazine (2.29 g, 20 mM); the reaction was stirred for 24 hours and then poured on to water (200 ml). The aqueous layer was extracted with ether (3×100 ml), the combined organic phases washed with water (100 ml) and dried. Removal of the solvents under reduced pressure followed by recrystallisation gave the title compound (1.3 g), m.p. 107°-8° C.

Workup

  1. extractionThe aqueous layer was extracted with ether (3×100 ml)
  2. washthe combined organic phases washed with water (100 ml)
  3. customdried
  4. customRemoval of the solvents under reduced pressure
  5. customfollowed by recrystallisation

Sources & evidence

ORD record
ord-d7524eb1a1ae467999d9a5b38bbd27a5
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

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