Aniline → HCID 68835672, compound

HRID 222850Notes

Reaction equation

HRID 222850 reaction equation
[N:1]1([C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Br.C(=O)([O-])[O-].[K+].[K+].NC1C=CC=CC=1>CN(C=O)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH:9][C:8]1[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=1[N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 4587952-(Piperidin-1-yl)anilineHCID 40672073-Methoxybenzyl bromide

Product 1

HCID 68835672HCID 68835672, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1 g of 2-piperidinoaniline in 10 mL of DMF are added 795 μL of 3-methoxybenzyl bromide (1 equivalent) and 1.57 g of potassium carbonate (2 equivalents). The whole is heated to 100° C. for 2-3 hrs, until disappearance of the starting aniline. The medium is poured onto ice and then extracted with ethyl acetate. The organic phase washed with water is dried on magnesium sulfate, filtered and evaporated under reduced pressure. By silica gel chromatography of the residue (cyclohexane/ethyl acetate: 99/1) 1.46 g of the desired product may be isolated.

Workup

  1. additionThe medium is poured onto ice
  2. extractionextracted with ethyl acetate
  3. washThe organic phase washed with water
  4. customis dried on magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-36555b6cf1c348818f93bff1d6525de2
Source dataset
uspto-grants-2012_06
Patent number
US08207373B2

Reaction notes

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