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

HRID 2113527Notes

Reaction equation

HRID 2113527 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-ebb5fec2d1c241c5a9e9919d3cc2ed85
Source dataset
uspto-grants-2008_10
Patent number
US07432270B2

Reaction notes

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