Hydrochloric Acid → 1-[2-(Diphenylmethoxy)ethyl]piperazine

HRID 565631Notes

Reaction equation

HRID 565631 reaction equation
[CH:1]([OH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.Cl>C1(C)C=CC=CC=1>[C:2]1([CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:14][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7037BenzhydrolHCID 76771-(2-Hydroxyethyl)piperazineHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

Product 1

HCID 6485251-[2-(Diphenylmethoxy)ethyl]piperazineYield 24%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a reactor equipped with a water trap (Dean-Stark trap), a mixture of benzhydrol (5.0 g), 1-(2-hydroxyethyl)piperazine (3.5 g), camphor-10-sulfonic acid (14 g), and toluene (80 mL) was refluxed for 6 hours. Then, 1N-hydrochloric acid was added and the mixture was separated into two phases. The aqueous layer was made basic with 5 N aqueous sodium hydroxide, saturated with sodium chloride, and extracted with chloroform. The extract was washed with a small amount of saturated aqueous NaCl, dried over MgSO4, and concentrated under reduced pressure to provide 1.9 g of the title compound. Yield 24%. This compound was not further purified but directly submitted to the next reaction.

Workup

  1. customIn a reactor equipped with a water trap (Dean-Stark trap)
  2. temperaturewas refluxed for 6 hours
  3. customthe mixture was separated into two phases
  4. extractionextracted with chloroform
  5. washThe extract was washed with a small amount of saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-00c1c6630ecf47208eb3f1c7ebf7a44f
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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