2-Chloroethyl methyl sulfide → 1-(2-Methylsulfanylethyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

HRID 32165

Reaction equation

[CH3:1][C:2]1([CH3:22])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:3]1.[CH3:23][S:24][CH2:25][CH2:26]Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:23][S:24][CH2:25][CH2:26][N:19]1[CH2:18][CH2:17][N:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:4]2[CH2:3][C:2]([CH3:22])([CH3:1])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5]2)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the 1-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (100 mg, 0.333 mmol) produced in Example (8b), 2-chloroethyl methyl sulfide (38.7 mg, 0.349 mmol), potassium carbonate (78.2 mg, 0.566 mmol) and acetonitrile (2 mL) was stirred for 8 hours and 30 minutes at an external temperature of 80° C. The reaction mixture was concentrated and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 88 mg of 1-(2-methylsulfanylethyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine as a colorless solid.

Workup

concentrationThe reaction mixture was concentrated
customthe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record: ord-bd9582084aa347fba5c296a15048dd4a
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425554B2

Linked notes

Loading…