Triethylamine → 1-Methanesulfonyl-N-(5-phenyl-2-pyrazinyl)spiro[indoline-3,4'-piperidine]-1'-carboxamide

HRID 635897Notes

Reaction equation

HRID 635897 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([NH:13][C:14](=[O:22])OC3C=CC=CC=3)=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:24][S:25]([N:28]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:30]2([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH2:29]1)(=[O:27])=[O:26].CCN(CC)CC>C(Cl)(Cl)Cl.CCOC(C)=O>[CH3:24][S:25]([N:28]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:30]2([CH2:31][CH2:32][N:33]([C:14]([NH:13][C:10]3[CH:9]=[N:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:12][N:11]=3)=[O:22])[CH2:34][CH2:35]2)[CH2:29]1)(=[O:26])=[O:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9879110Phenyl 5-phenylpyrazin-2-ylcarbamateHCID 219560841-(Methylsulfonyl)spiro[indoline-3,4'-piperidine] hydrochloride

Product 1

HCID 121087811-Methanesulfonyl-N-(5-phenyl-2-pyrazinyl)spiro[indoline-3,4'-piperidine]-1'-carboxamideYield 93%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of phenyl N-(5-phenyl-2-pyrazinyl)carbamate 1-2 (7,350 mg, 1.20 mmol), 1-methylsulfonylspiro[indoline-3,4′-piperidine]hydrochloride 1-3 (400 mg, 1.32 mmol) and Et3N (0.5 mL, 3.6 mmol) in CHCl3 (6 mL) was heated to reflux for 3 h. After cooling, the mixture was diluted with EtOAc, washed with 10% citric acid, sat. NaHCO3 and brine, dried over MgSO4, and concentrated under reduced pressure to start precipitation. The precipitate was collected by filtration and dried in vacuo to give 100 (517 mg, 93%) as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. temperatureAfter cooling
  4. washwashed with 10% citric acid, sat. NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customprecipitation
  8. filtrationThe precipitate was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-4a603e2b761049f69bfff232b6942878
Source dataset
uspto-grants-2001_02
Patent number
US06191160B1

Reaction notes

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