2-Chloroethanol → HCID 21545604, compound

HRID 1605958Notes

Reaction equation

HRID 1605958 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:4][CH:3]=1.[CH2:14](Cl)[CH2:15][OH:16].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(O)C>[OH:16][CH2:15][CH2:14][N:11]1[CH2:10][CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 1977484-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 21545604HCID 21545604, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.77 g of 4-(p-fluorophenyl)-1,2,3,6-tetrahydropyridine, 0.8 g. of ethylene chlorohydrin, 1.2 g. of sodium carbonate and a few crystals of sodium iodide are heated under reflux conditions in 10 ml. of ethanol for 24 hours and filtered hot and the filtrate is evaporated to dryness. The residual oil is purified by column chromatography on silica gel with acetic acid ethyl ester-ethanol (1:1) as eluting agent. The 1-(2-hydroxyethyl)-4-(p-fluorophenyl)-1,2,3,6-tetrahydropyridine obtained from the eluate melts at 96°-98°C. after recrystallization from cyclohexane.

Workup

  1. filtrationfiltered hot
  2. customthe filtrate is evaporated to dryness
  3. customThe residual oil is purified by column chromatography on silica gel with acetic acid ethyl ester-ethanol (1:1)
  4. washas eluting agent

Sources & evidence

ORD record
ord-215179dc33184f4d8c28472eb59b2f39
Source dataset
uspto-grants-1976_04
Patent number
US03951987

Reaction notes

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