Piperidin-2-ylmethanol → 1-(2-Chlorophenylthiocarbamoyl)-2-hydroxymethylpiperidine

HRID 654399Notes

Reaction equation

HRID 654399 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]=[C:17]=[S:18]>O1CCCC1.C(N(CC)CC)C>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]([N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:3]1[CH2:2][OH:1])=[S:18]

Participants

5

Reactant 2

HCID 94263Piperidin-2-ylmethanolHCID 1231711-Chloro-2-isothiocyanatobenzene

Product 1

HCID 198871821-(2-Chlorophenylthiocarbamoyl)-2-hydroxymethylpiperidine

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.4 g 2-Hydroxymethylpiperidine in 50 ml absolute tetrahydrofuran was treated with 1 drop of triethylamine and 5 g 2-chlorophenyl isothiocyanate. After 12 hours at room temperature, the reaction solution was cooled in an ice bath. The crystals were suction filtered and recrystallised from ethyl acetate.

Workup

  1. temperaturethe reaction solution was cooled in an ice bath
  2. filtrationfiltered
  3. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-8616189f40e2434a86775450bfd36dcc
Source dataset
uspto-grants-1992_07
Patent number
US05131946

Reaction notes

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