3-Bromo-1-propanol → HCID 58056349, compound

HRID 1773499Notes

Reaction equation

HRID 1773499 reaction equation
[N:1]1([C:7]2[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][C:8]=2[NH2:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][OH:21]>CN(C)C=O>[NH2:14][C:8]1[C:7]([N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[C:12]([NH:13][CH2:18][CH2:19][CH2:20][OH:21])[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 24758Sodium hydrideHCID 54256089HCID 54256089, compound

Product 1

HCID 58056349HCID 58056349, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-piperidin-1-yl-benzene-1,3-diamine (300 mg, 1.57 mmol) in N,N-dimethylformamide (4 mL) was added sodium hydride (60% suspension in mineral oil, 63 mg, 1.57 mmol) followed by 3-bromo-1-propanol (0.14 mL, 1.57 mmol) and the reaction mixture was stirred at 60° C. overnight. The resulting mixture was then extracted with ethyl acetate (150 mL) and the organic layer was washed twice with water (80 mL) and once with brine (80 mL), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 60/40) to give 22 mg of 3-(3-amino-2-piperidin-1-yl-phenylamino)-propan-1-ol.

Workup

  1. extractionThe resulting mixture was then extracted with ethyl acetate (150 mL)
  2. washthe organic layer was washed twice with water (80 mL) and once with brine (80 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 60/40)

Sources & evidence

ORD record
ord-1b75d76ee2a64b3b97fcc175eaab859f
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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