Carbon Disulfide → [3-[3-(1-Piperidinylmethyl)phenoxy]propyl]isothiocyanate

HRID 35067

Reaction equation

[C:1](=[S:3])=S.[N:4]1([CH2:10][C:11]2[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=2)[O:14][CH:15](N)[CH2:16][CH3:17])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C([N:24](CC)CC)C>CC(C)=O.[Hg](Cl)Cl>[N:4]1([CH2:10][C:11]2[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=2)[O:14][CH2:15][CH2:16][CH2:17][N:24]=[C:1]=[S:3])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

Conditions

Temperature: -14 °C

Procedure

A solution of carbon disulphide (3.3 ml) in acetone (8 ml) was added dropwise to a solution of 3-[3-(1-piperidinylmethyl)phenoxy propanamine (12.4 g) in acetone (30 ml) over a 15 minute period, between -5° and -10° C. The solution was cooled to -14° C. and mercury (II) chloride (13.6 g) in acetone (30 ml) was added, during 45 minutes. Triethylamine (16 ml) was added at 0° C. during 15 minutes, and the mixture was heated at reflux for 45 minutes. The resulting suspension was purified by filtration and the filtrate evaporated in vacuo. The residue was purified by column chromatography using methanol as eluant to give the title compound (6 g) as an amber oil.

Workup

temperaturethe mixture was heated
temperatureat reflux for 45 minutes
filtrationThe resulting suspension was purified by filtration
customthe filtrate evaporated in vacuo
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-c5fa03e0c1ec46999ab8fa5c993f6693
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04764612

Linked notes

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