Benzene, (2-bromoethoxy)- → HCID 19085450, compound

HRID 962466Notes

Reaction equation

HRID 962466 reaction equation
[C:1]1([O:7][CH2:8][CH2:9]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][OH:18])[CH2:12]1.C(=O)(O)[O-].[Na+]>>[O:7]([CH2:8][CH2:9][N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][OH:18])[CH2:12]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 68526Benzene, (2-bromoethoxy)-HCID 107308Piperidin-3-ylmethanolHCID 516892Sodium Bicarbonate

Product 1

HCID 19085450HCID 19085450, compound

Procedure

A mixture of 2-bromoethyl phenyl ether (20.1 g), piperidin-3-yl-methanol (11.5 g), sodium bicarbonate (8.4 g) and IMS (100 ml) was boiled under reflux for 16 hours. The mixture was evaporated to dryness under reduced pressure and the residue was treated with water (50 ml), 2M sodium hydroxide solution (20 ml) and extracted with dichloromethane. The combined dichloromethane extracts were washed with brine and then extracted with 2M hydrochloric acid. The combined acidic extracts were washed with dichloromethane then basified with 2M sodium hydroxide solution and then extracted with dichloromethane to give 1-(2-phenoxyethyl)piperidin-3-ylmethanol as an oil.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. additionthe residue was treated with water (50 ml), 2M sodium hydroxide solution (20 ml)
  4. extractionextracted with dichloromethane
  5. washThe combined dichloromethane extracts were washed with brine
  6. extractionextracted with 2M hydrochloric acid
  7. washThe combined acidic extracts were washed with dichloromethane
  8. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-1e9cfaccd6784e07bae2ccf793dfe239
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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