1,1'-Carbonyldiimidazole → HCID 59856533, compound

HRID 469353Notes

Reaction equation

HRID 469353 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[NH2:13][C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:21][CH2:22][NH:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:26][CH2:25]1>CN(C=O)C>[CH2:30]([N:27]1[CH2:28][CH2:29][CH:24]([N:23]2[CH2:22][CH2:21][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([F:20])[C:14]=3[NH:13][C:6]2=[O:7])[CH2:25][CH2:26]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59856532HCID 59856532, compound

Product 1

HCID 59856533HCID 59856533, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

11.0 g (65.8 mmol) CDI were added to 13.1 g (40.0 mmol) [2-(2-amino-3-fluoro-phenyl)-ethyl]-(1-benzyl-piperidin-4-yl)-amine in 120 mL DMF. The mixture was heated to 100° C. and stirred for 1 h. After the reaction mixture had cooled to RT it was poured onto 300 mL ice water. The aqueous phase was extracted several times with DCM, the organic phases were combined, dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was purified by flash chromatography. The fractions containing the product were combined and evaporated down.

Workup

  1. temperatureAfter the reaction mixture had cooled to RT it
  2. extractionThe aqueous phase was extracted several times with DCM
  3. customdried on magnesium sulphate
  4. filtrationfiltered
  5. customevaporated down i
  6. customThe residue was purified by flash chromatography
  7. additionThe fractions containing the product
  8. customevaporated down

Sources & evidence

ORD record
ord-13b41da24e90427ebc4197855d654017
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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