Piperidine → HCID 59250078, compound

HRID 2191516Notes

Reaction equation

HRID 2191516 reaction equation
[CH3:1][C:2]1[C:6]2[C:7](=[O:20])[N:8]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH2:9][CH2:10][CH2:11][C:5]=2[NH:4][C:3]=1C=O.FC1C=CC(CS(C2C=C3C(=CC=2)NC(=O)C3)(=O)=O)=CC=1.N1CCCCC1>C(O)C>[CH3:1][C:2]1[C:6]2[C:7](=[O:20])[N:8]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[CH2:9][CH2:10][CH2:11][C:5]=2[NH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 18179638HCID 18179638, compoundHCID 592500683-Methyl-5-(2-morpholin-4-yl-ethyl)-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde

Product 1

HCID 59250078HCID 59250078, compoundYield 166.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methyl-5-(2-morpholin-4-yl-ethyl)-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 10c (80 mg, 0.26 mmol) and 5-(4-fluoro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one 65a (72 mg, 0.24 mmol) were dissolved in 2.5 ml of ethanol, and added with 42 μA of piperidine the solution at room temperature. Upon completion of the addition, the reaction mixture was heated to reflux for 3 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (3 ml×2) and dried to obtain the title compound (Z)-2-(5-(4-fluorobenzylsulfonyl)-2-oxoindolin-3-ylidene)methyl)-3-methyl-5-(2-morpholinoethyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 69 (120 mg, yield 85.7%) as an orange solid.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 3 hours
  4. filtrationfiltered
  5. washThe filter cake was washed with anhydrous ethanol (3 ml×2)
  6. customdried

Sources & evidence

ORD record
ord-8465397dbea34bbda6975eadf708c25a
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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