Réaction #46374

Équation de réaction

(RS) 2-aminomethyl-piperidine-1-carboxylic acid tert butyl ester

Benzoyl chloride

sodium thiocyanate

→

title product

Rendement 76.4%

2-Thioureidomethyl-piperidine-1-carboxylic acid tert butyl ester

Rendement 76.4%

Solvants

acetone

acetone

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONWhen the addition
2. 2
   Températurewas refluxed for 15 minutes
3. 3
   TempératureThe mixture was refluxed for 2 hours
4. 4
   Températurecooled to room temperature
5. 5
   Autresolvent removed at reduced pressure
6. 6
   Autrechromatographed (silica gel, 0-10% (9:1 methanol/ammonia) in dichloromethane eluant)

Mode opératoire

Benzoyl chloride (1.2 ml) was added dropwise to sodium thiocyanate (0.90 g) in acetone (50 ml). When the addition was complete the mixture was refluxed for 15 minutes, cooled to room temperature and (RS) 2-aminomethyl-piperidine-1-carboxylic acid tert butyl ester (2.0 g) in acetone (5 ml) added. The mixture was refluxed for 2 hours, cooled to room temperature and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, 0-10% (9:1 methanol/ammonia) in dichloromethane eluant) to give the title product (1.95 g).

Source