Triethylamine → 1-methanesulfonyl-N-(1-phenyl-4-piperidyl)spiro[indoline-3,4'-piperidine]-1'-carboxamide

HRID 1271616Notes

Reaction equation

HRID 1271616 reaction equation
Cl.[CH3:2][S:3]([N:6]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:7]1)(=[O:5])=[O:4].C(N(CC)CC)C.[C:27]1([N:33]2[CH2:38][CH2:37][CH:36]([NH:39][C:40](=O)[O:41]C3C=CC=CC=3)[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:2][S:3]([N:6]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]2([CH2:9][CH2:10][N:11]([C:40]([NH:39][CH:36]3[CH2:37][CH2:38][N:33]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:34][CH2:35]3)=[O:41])[CH2:12][CH2:13]2)[CH2:7]1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 219560841-(Methylsulfonyl)spiro[indoline-3,4'-piperidine] hydrochlorideHCID 22936218HCID 22936218, compound

Product 1

HCID 229362231-methanesulfonyl-N-(1-phenyl-4-piperidyl)spiro[indoline-3,4'-piperidine]-1'-carboxamideYield 31.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-Methanesulfonyl-spiro[indoline-3,4′-piperidine] hydrochloride (37 mg) and triethylamine (170 μL) were added to a solution of phenyl N-(1-phenyl-4-piperidyl)carbamate (36 mg) in chloroform (3 mL), and the mixture was heated to reflux for 15 hours. The reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was crystallized from diethyl ether to give the title compound (18 mg) as a colorless crystal.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 15 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-36c83ac409744c73b3f00b96ca188e3e
Source dataset
uspto-grants-2007_04
Patent number
US07205417B2

Reaction notes

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