Benzoyl chloride → 2-Thioureidomethyl-piperidine-1-carboxylic acid tert butyl ester

HRID 2074396Notes

Reaction equation

HRID 2074396 reaction equation
C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[Na+].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][NH2:28])=[O:20])([CH3:17])([CH3:16])[CH3:15]>CC(C)=O>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][NH:28][C:11]([NH2:12])=[S:10])=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 516871Sodium thiocyanateHCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylate

Product 1

HCID 865936762-Thioureidomethyl-piperidine-1-carboxylic acid tert butyl esterYield 76.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

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).

Workup

  1. additionWhen the addition
  2. temperaturewas refluxed for 15 minutes
  3. temperatureThe mixture was refluxed for 2 hours
  4. temperaturecooled to room temperature
  5. customsolvent removed at reduced pressure
  6. customchromatographed (silica gel, 0-10% (9:1 methanol/ammonia) in dichloromethane eluant)

Sources & evidence

ORD record
ord-dcd57394355342859d90eb3f1511b8d9
Source dataset
uspto-grants-2011_04
Patent number
US07919507B2

Reaction notes

Loading…