2-Chloroethanol → 4-((4-Chlorophenyl)phenylmethyl)-1-piperazineethanol

HRID 661319Notes

Reaction equation

HRID 661319 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][OH:24].[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:22][CH2:23][OH:24])[CH2:13][CH2:14]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 4875Potassium IodideHCID 9340NorchlorcyclizineHCID 10340Sodium Carbonate

Product 1

HCID 34198984-((4-Chlorophenyl)phenylmethyl)-1-piperazineethanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

Levorotatory (−)-1-[(4-chlorophenyl)phenylmethyl]piperazine (50 gm), 2-chloroethanol (31.4 gm), potassium iodide (1.3 gm) and sodium carbonate (40.8 gm) are taken in toluene (446 ml) and refluxed for 24 hours. The reaction mixture is cooled to 25-35° C., washed with water (285 ml) followed by two times with water (each time 185 ml). The layers are separated. Toluene is evaporated from organic layer under reduced pressure to yield 58 gm of levorotatory (−)-[2-[4-[(4-Chlorophenyl)-phenylmethyl]-1-piperazinyl]ethanol.

Workup

  1. temperaturerefluxed for 24 hours
  2. washwashed with water (285 ml)
  3. customThe layers are separated
  4. customToluene is evaporated from organic layer under reduced pressure

Sources & evidence

ORD record
ord-2cf9d72c04ef4c499d1e7e9fda83c435
Source dataset
uspto-grants-2011_12
Patent number
US08084606B2

Reaction notes

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