1-(2-Hydroxyethyl)piperazine → 1-(2-Hydroxyethyl)-4-[(2-methoxyphenyl)methyl]piperazine

HRID 1081266Notes

Reaction equation

HRID 1081266 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.[OH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(O)C>[OH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[O:2][CH3:1])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 814952-(Chloromethyl)anisole

Product 1

HCID 233639681-(2-Hydroxyethyl)-4-[(2-methoxyphenyl)methyl]piperazineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methoxybenzyl chloride (16 g) and 1-(2-hydroxyethyl)piperazine (13 g) in ethanol (50 ml) were heated under reflux for 4 hours. The solvent was removed under vacuum and the resulting oil was passed through a pad of silica gel eluting with 10% methanol-ammonia in dichloromethane to give 1-(2-hydroxyethyl)-4-[(2-methoxyphenyl)methyl]piperazine as a colourless oil (80%), 13C nmr (CDCl3) 157.4, 130.3, 127.8, 125.2, 119.8, 110.0, 59.5, 57.6, 55.2, 54.8, 52.7 and 52.4 ppm. This material (15 g) was treated at 0° C. with thionyl chloride (15 ml). The mixture was then heated at reflux for 2 hours. Toluene was added and the mixture was evaporated under reduced pressure. The resulting solid was collected and washed thoroughly to give the dihydrochloride of the title compound as a white solid, m.p. 276°-279° C. (dec.).

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-94ff7b35d8e6476b98d6e4e8de12d532
Source dataset
uspto-grants-1996_12
Patent number
US05585378

Reaction notes

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