Water → HCID 19863408, compound

HRID 1164957Notes

Reaction equation

HRID 1164957 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].Cl[CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]1.O>CN(C)C=O>[CH3:23][CH:20]1[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][CH2:14][S:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 158094-NitrobenzenethiolHCID 14210661HCID 14210661, compound

Product 1

HCID 19863408HCID 19863408, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve 8.50 g (55 mmol) of 4-nitrothiophenol in 40 mL of dimethylformamide and make basic with 13.7 mL of 4N potassium hydroxide. Add 10.60 g (60 mmol) of N-[3-chloropropyl]-4-methylpiperidine and heat this solution to 100° C. for 3 h. After this time cool the reaction to room temperature. Add 200 mL of water and extract with 2×150 mL of methylene chloride. Acidify the combined organic extracts to pH=1 with 1N hydrochloric acid and extract with 4×150 mL of water. Neutralize the combined aqueous extracts with saturated sodium bicarbonate solution and extract with 3×200 mL of methylene chloride. Dry the organic extracts over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to provide the title compound.

Workup

  1. temperatureAfter this time cool
  2. customthe reaction to room temperature
  3. extractionextract with 2×150 mL of methylene chloride
  4. extractionextract with 4×150 mL of water
  5. extractionextract with 3×200 mL of methylene chloride
  6. dry with materialDry the organic extracts over anhydrous sodium sulfate
  7. filtrationFilter the drying agent
  8. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-f5be6ab6f052473abfd4d5ef0f0e0443
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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