Water → HCID 20542615, compound

HRID 2285915Notes

Reaction equation

HRID 2285915 reaction equation
[C:1]1([C:7]2([OH:13])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1.O>CS(C)=O>[C:1]1([C:7]2([O:13][C:17]3[CH:22]=[N:21][CH:20]=[CH:19][N:18]=3)[CH2:12][CH2:11][NH:10][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 963874-Phenylpiperidin-4-ol

Product 1

HCID 20542615HCID 20542615, compoundYield 3.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 4-phenyl-4-piperidinol (7.1 g, 40 mM), DMSO (50 ml) and sodium hydride (2 g of a 50% dispersion in oil) was heated at 80° until homogenous, cooled to room temperature and treated with chloropyrazine (4.6 g, 40 mM) in DMSO (10 ml). After 24 hours the reaction mixture was poured on to water (250 ml) and extracted with toluene (2×250 ml). The combined organic phases were washed with brine, dried and the solvents removed under reduced pressure. Sublimation of the residue at 0.1 mm Hg (bath temp. 100°) gave the title compound (400 mg) m.p. 107°-8°.

Workup

  1. temperaturewas heated at 80° until homogenous,
  2. extractionextracted with toluene (2×250 ml)
  3. washThe combined organic phases were washed with brine
  4. customdried
  5. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-5df898de87a048f4833025601754228a
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

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