Water → 1-Acetyl-4-[4-(3-hydroxypropyloxy)phenyl]piperazine

HRID 1816722Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[CH2:18][CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(Cl)Cl>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:18][CH2:19][CH2:20][OH:21])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-acetyl-4-(4-hydroxyphenyl)piperazine (3.00 g) in N,N-dimethylformamide was treated with 3-bromo-1-propanol (1.60 ml) and potassium carbonate (2.82 g), and the mixture was heated at 60° C. for 8 hours. Then 3-bromo-1-propanol (1.60 ml) was added again, and the mixture was heated at 110° C. for 6 hours. After cooling, water and methylene chloride were added to the reaction mixture, and the organic layer was taken and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography eluting with a mixed solvent of methylene chloride-methanol (from 0% to 6% gradient elution) to give 1-acetyl-4-[4-(3-hydroxypropyloxy)phenyl]piperazine (3.53 g) as a pale pink solid.

Workup

temperaturethe mixture was heated at 110° C. for 6 hours
temperatureAfter cooling
dry with materialdried over magnesium sulfate
filtrationMagnesium sulfate was filtered off
customthe filtrate was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography
washeluting with a mixed solvent of methylene chloride-methanol (from 0% to 6% gradient elution)

Sources & evidence

ORD record: ord-1e9b80f76b40498ab5f127ab44db2c62
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884868B1

Reaction notes

Loading…