1-(2-Hydroxyethyl)piperazine → 2-[4-[(4-Methylsulfanylphenyl)methyl]piperazin-1-yl]ethanol

HRID 2309032Notes

Reaction equation

HRID 2309032 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[OH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(O)C>[OH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 8471TriethylamineHCID 701281-(Chloromethyl)-4-(methylthio)benzene

Product 1

HCID 20575972-[4-[(4-Methylsulfanylphenyl)methyl]piperazin-1-yl]ethanolYield 71.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(methylthio)benzyl chloride (28.6 g), 1-(2-hydroxyethyl)piperazine (21.6 g), triethylamine (16.8 g), and ethanol (250 ml) is stirred at room temperature for 5 hours. The ethanol is then removed in vacuo and water added to the residue. The product is extracted with ether, dried, and the ether evaporated to give 31.6 g of 1-(2-hydroxyethyl)-4-[4-(methylthio)benzyl] piperazine as an orange oil, suitable for use in the next reaction.

Workup

  1. customThe ethanol is then removed in vacuo and water
  2. additionadded to the residue
  3. extractionThe product is extracted with ether
  4. customdried
  5. customthe ether evaporated

Sources & evidence

ORD record
ord-5e33a732aad4425ba516fd9cf0aaad75
Source dataset
uspto-grants-1987_09
Patent number
US04692448

Reaction notes

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