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

HRID 325713Notes

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-7e9628edab16419cb23c7252de072493
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04442110

Reaction notes

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