Chlorosuccinimide → HCID 90338520, compound

HRID 1509042Notes

Reaction equation

HRID 1509042 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]3[CH2:14][CH2:15][CH2:16][C:11]3=[C:10]([NH2:17])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:18]N1C(=O)CCC1=O>CN(C=O)C.O.C(OCC)(=O)C>[Cl:18][C:9]1[C:10]([NH2:17])=[C:11]2[CH2:16][CH2:15][CH2:14][C:12]2=[N:13][C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

6

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 118037003HCID 118037003, compound

Product 1

HCID 90338520HCID 90338520, compoundYield 38.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 25-mL round bottom flask was charged with 2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-amine (0.250 g, 1.02 mmol) in DMF (6 mL). N-Chlorosuccinimide (0.136 g, 1.02 mmol) was added at rt and the resultant solution was stirred for 3 h. Further N-chlorosuccinimide (0.036 g, 0.27 mmol) was added and the reaction was stirred for 2 h. The reaction was diluted with water (100 mL) and ethyl acetate (50 mL). The layers were separated and the aqueous layer extracted with ethyl acetate (2×25 mL). The combined extract acetate extract was washed with saturated sodium chloride (2×10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using hexanes/ethyl acetate (10:0 to 9:1) as the eluent to afford the title compound (0.110 g, 38%) as a white solid. MW=279.16. 1H NMR (CD3, 500 MHz) δ 7.62-7.59 (m, 1H), 7.52-7.48 (m, 1H), 7.37-7.32 (m, 2H), 4.54 (s, 2H), 2.99 (t, J=7.5 Hz, 2H), 2.80 (t, J=7.5 Hz, 2H), 2.21 (quin, J=7.5 Hz, 2H); ESI MS m/z 279 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with ethyl acetate (2×25 mL)
  3. extractionThe combined extract acetate
  4. extractionextract
  5. washwas washed with saturated sodium chloride (2×10 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1f0ba7bbb5814e6690d400c491ed2177
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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