Water → HCID 18952131, compound

HRID 1492224Notes

Reaction equation

HRID 1492224 reaction equation
[N:1]1([C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:14](Cl)(Cl)=[S:15].O>O1CCOCC1>[N:1]1([C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=[C:14]=[S:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962Water2×HCID 10040ThiophosgeneHCID 4587952-(Piperidin-1-yl)aniline

Product 1

HCID 18952131HCID 18952131, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-piperidinoaniline (17.6 g) in dioxane (100 ml) was added over 25 minutes to a mixture of thiophosgene (10.2 ml) and water (200 ml) which had been cooled to 0° C. The temperature of the mixture was allowed to rise to ambient and the mixture was stirred for 4 hours. Ice (200 g) and water (200 ml) were added and the mixture extracted with ether (6×50 ml). The combined extracts were washed with water (100 ml) and brine (100 ml), dried and evaporated to give a residue which purified by chromatography on a silica column eluted with hexane to give 2-piperidinophenyl isothiocyanate as an oil.

Workup

  1. extractionthe mixture extracted with ether (6×50 ml)
  2. washThe combined extracts were washed with water (100 ml) and brine (100 ml)
  3. customdried
  4. customevaporated
  5. customto give a residue which
  6. custompurified by chromatography on a silica column
  7. washeluted with hexane

Sources & evidence

ORD record
ord-cff881171fad4776805a324cdac249f6
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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