Piperidine → HCID 86640165, compound

HRID 2191518Notes

Reaction equation

HRID 2191518 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][C:9]2[NH:13][C:14](C=O)=[C:15]([CH3:16])[C:8]=2[C:7]1=[O:19])[CH3:2].FC1C=CC(CS(C2C=C3C(=CC=2)NC(=O)C3)(=O)=O)=CC=1.N1CCCCC1>C(O)C>[CH2:20]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][C:9]2[NH:13][CH:14]=[C:15]([CH3:16])[C:8]=2[C:7]1=[O:19])[CH3:21]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 18179638HCID 18179638, compoundHCID 592500815-(2-Diethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde

Product 1

HCID 86640165HCID 86640165, compoundYield 132%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(2-Diethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 1j (60 mg, 0.21 mmol) and 5-(4-fluoro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one 65a (58 mg, 0.19 mmol) were dissolved in 2 ml of ethanol, and added with 34 μl 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)-5-(2-(diethylamino)ethyl)-3-methyl-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 71 (73 mg, yield 66%) 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-6857192f6bc44b28a92c23d451680cff
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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