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

HRID 35067
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 212975763-(1-Piperidinylmethyl)phenoxy propanamine

Product 1

HCID 13391620[3-[3-(1-Piperidinylmethyl)phenoxy]propyl]isothiocyanate

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalyst
HCID 180
Acetone
Solvent
3×

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

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 45 minutes
  3. filtrationThe resulting suspension was purified by filtration
  4. customthe filtrate evaporated in vacuo
  5. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes