1-((1R,2R)-2-(1-benzylpiperidin-3-ylamino)cyclohexyl)-3-phenylurea → 1-phenyl-3-((1R,2R)-2-(piperidin-3-ylamino)cyclohexyl)urea

HRID 2369968Notes

Reaction equation

HRID 2369968 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C@@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]2[NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:23])[CH2:9]1)C1C=CC=CC=1.[H][H]>Cl.[OH-].[OH-].[Pd+2].CO>[C:25]1([NH:24][C:22]([NH:21][C@@H:16]2[CH2:17][CH2:18][CH2:19][CH2:20][C@H:15]2[NH:14][CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[O:23])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 2

HCID 712356561-((1R,2R)-2-(1-benzylpiperidin-3-ylamino)cyclohexyl)-3-phenylureaHCID 178418361HCID 178418361, compound

Product 1

HCID 712273541-phenyl-3-((1R,2R)-2-(piperidin-3-ylamino)cyclohexyl)ureaYield 96.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a PARR shaker was added 1-((1R,2R)-2-(1-benzylpiperidin-3-ylamino)cyclohexyl)-3-phenylurea (1.4 g, 3.44 mmol), Pd(OH)2 (0.484 g, 3.44 mmol), MeOH (20 mL) and 3 drops of 1N HCl. The reaction vessel charged with hydrogen and the pressure was maintained at 30 psi with shaking overnight. After this time, the reaction was filtered through CELITE® and the filtrate was concentrated to give the product, 1-phenyl-3-((1R,2R)-2-(piperidin-3-ylamino)cyclohexyl)urea (1.05 g, 3.32 mmol, 96% yield), as an off white solid. It was used in the next step without further purification. Anal. Calcd. for C18H28N4O m/z 316, found: 317.3 (M+H)+; 1H NMR (500 MHz, methanol-d3) δ ppm 7.35 (d, J=7.70 Hz, 2H), 7.24 (t, J=7.42 Hz, 2H), 6.97 (t, J=7.42 Hz, 1H), 3.49-3.37 (m, 1H), 3.16-3.03 (m, 1H), 2.94-2.83 (m, 1H), 2.70 (td, J=9.35, 4.95 Hz, 1H), 2.57-2.47 (m, 1H), 2.47-2.39 (m, 1H), 2.39-2.25 (m, 1H), 2.10-1.90 (m, 3H), 1.79-1.68 (m, 3H), 1.58-1.43 (m, 1H), 1.39-1.16 (m, 5H).

Workup

  1. temperaturethe pressure was maintained at 30 psi
  2. filtrationAfter this time, the reaction was filtered through CELITE®
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-719d9ae8970f4589a3609627c9110f25
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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