2-Chloroethanol → Acetyl-dibenzyl-glycolic-acid beta-(4-phenyl-piperidino)-ethyl ester oxalate

HRID 2419121Notes

Reaction equation

HRID 2419121 reaction equation
Cl[CH2:2][CH2:3][OH:4].[C:5](=[O:8])([O-:7])[O-:6].[K+].[K+].[C:11]1([CH:17]2[CH2:22][CH2:21]N(CC[OH:25])CC2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:26]1([CH:32]2[CH2:37][CH2:36][N:35]([CH2:38][CH2:39]Cl)[CH2:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[OH2:41]>C(Cl)(Cl)Cl>[C:3]([OH:4])(=[O:25])[C:5]([OH:7])=[O:8].[C:26]1([CH:32]2[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][O:6][C:5](=[O:8])[C:22]([CH2:17][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)([CH2:21][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:41][C:3](=[O:4])[CH3:2])[CH2:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 5

HCID 342-ChloroethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 2648322-(4-Phenylpiperidin-1-yl)ethanolHCID 131954071-(2-Chloroethyl)-4-phenylpiperidine

Product 1

HCID 86735883Acetyl-dibenzyl-glycolic-acid beta-(4-phenyl-piperidino)-ethyl ester oxalate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

75 g. (0.46 mol) β-4-phenylpiperidine is heated with 38 g. (0.46 mol) 2-chloroethanol for 5 hours at about 120° C. After cooling, the reaction mixture is dissolved in 500 ml. water, rendered alkaline with potassium carbonate, extracted with 1 liter ether, dried, evaporated and the residue distilled in a high vacuum. There is obtained 55 g. (61% of theory) β-(4-phenyl-piperidino)-ethanol (b.p. 155° C./0.2 mm.Hg.), which is dissolved in 500 ml. chloroform. The corresponding hydrochloride is then precipitated out by the addition of dry hydrogen chloride. 50 ml. thionyl chloride is added and the reaction mixture heated under reflux for 5 hours and cooled. The precipitated product is filtered off, dissolved in 300 ml. water and rendered alkaline with 10N aqueous sodium hydroxide solution. The precipitated base is extracted with 500 ml. ether, dried and evaporated. There is obtained 45 g. (75% of theory) β-(4-phenyl-piperidino)-ethyl chloride.

Workup

  1. temperatureAfter cooling
  2. dissolutionthe reaction mixture is dissolved in 500 ml
  3. extractionextracted with 1 liter ether
  4. customdried
  5. customevaporated
  6. distillationthe residue distilled in a high vacuum
  7. customThere is obtained 55 g
  8. customThe corresponding hydrochloride is then precipitated out by the addition of dry hydrogen chloride
  9. additionthionyl chloride is added
  10. temperaturethe reaction mixture heated
  11. temperatureunder reflux for 5 hours
  12. temperaturecooled
  13. filtrationThe precipitated product is filtered off
  14. dissolutiondissolved in 300 ml
  15. extractionThe precipitated base is extracted with 500 ml
  16. dry with materialether, dried
  17. customevaporated
  18. customThere is obtained 45 g

Sources & evidence

ORD record
ord-f332c9443a5040b0b7117ae8f310bac6
Source dataset
uspto-grants-1978_08
Patent number
US04104380

Reaction notes

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