Potassium Carbonate → HCID 54098621, compound

HRID 362930Notes

Reaction equation

HRID 362930 reaction equation
Br[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:15]([NH:22][C:23](=[O:40])[NH:24][C:25]1[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]1)=[O:28])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CS(C)=O>[CH2:15]([NH:22][C:23](=[O:40])[NH:24][C:25]1[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][CH2:33][N:32]([CH:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:31]1)=[O:28])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 516892Sodium BicarbonateHCID 54111482HCID 54111482, compound

Product 1

HCID 54098621HCID 54098621, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Step 2): Bromodiphenylmethane (1.4 g, 5.6 mmol) was added to a solution of 2-(N'-n-heptylureido)-N-(piperidin-3-yl)benzamide (1.0 g, 2.8 mmol) and K2CO3 (0.4 g, 2.9 mmol) in DMSO (5 ml) at 0° C. The mixture was refluxed for 18 hours, poured into 1% NaHCO3 solution, extracted with ethyl acetate and washed with 1% NaHCO3 solution. The organic layer was dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel (25% to 50% ethyl acetate in hexane) to give 2-(N'-n-heptylureido)-N-(1-diphenylmethylpiperidin-3-yl)benzamide (0.3 g, 20.5%): mp 112° C. 1H NMR (CDCl3)ppm: 0.88 (3H, t), 1.23-1.35 (8H, m), 1.47-1.85 (6H, m), 2.05-2.20 (1H, m), 2.35-2.49 (1H, m), 2.57-2.80 (2H, m), 3.24 (2H, q), 4.12-4.23 (1H, m), 4.35 (1H, s), 4.57-4.65 (1H, m), 6.90-7.55 (14H, m), 8.48 (1H, d), 10.37 (1H, s).

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with 1% NaHCO3 solution
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (25% to 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ed458246f0e746ffa5d23ad4cf564535
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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