4-Aminophenol → HCID 67276379, compound

HRID 1807418Notes

Reaction equation

HRID 1807418 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=[CH:4]1)=[O:2].NC1C=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]2[CH2:33]CNCC2)=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[OH:20][C:17]1[CH:18]=[CH:11][C:12]([NH:8][C:1]([N:3]2[CH2:4][CH2:33][CH:28]([C:25]3[CH:24]=[CH:23][C:22]([Cl:21])=[CH:27][CH:26]=3)[CH2:6][CH2:7]2)=[O:2])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 4034-AminophenolHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 12036134-(4-Chlorophenyl)piperidine

Product 1

HCID 67276379HCID 67276379, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Carbonyldiimidazole (1.48 g) was added to a solution of 4-aminophenol (1.0 g) in DMF (10 ml) at 0° C. After 10 minutes, a mixture of 4-(4-chlorophenyl)piperidine (hydrochloride; 2.13 g), Hünig's base (1.18 g) and DMF (10 ml) was added. After two hours, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The product with the molecular weight of 330.82 (C18H19ClN2O2); MS (ESI): 331 (M+H+) was obtained in this way.

Workup

  1. additionwas added
  2. waitAfter two hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customMS (ESI): 331 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-e8423af8ff7c48b88190e0925a7e6402
Source dataset
uspto-grants-2013_01
Patent number
US08357686B2

Reaction notes

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