Allyl iodide → 3,5-Di-tert-butyl-2-[(allylamino)methyl]phenol

HRID 1173307

Reaction equation

HRID 1173307 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:9]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:8][C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:6][C:5]=1[OH:18].C([O-])(O)=O.[Na+].[CH2:24](I)[CH:25]=[CH2:26]>C(Cl)Cl>[C:10]([C:9]1[C:4]([CH2:3][NH:2][CH2:26][CH:25]=[CH2:24])=[C:5]([OH:18])[CH:6]=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:8]=1)([CH3:11])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 516892Sodium BicarbonateHCID 452597712-(Aminomethyl)-3,5-di-tert-butylphenol hydrochloride

Product 1

HCID 104235423,5-Di-tert-butyl-2-[(allylamino)methyl]phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.705 g (2.99 mmol) of the product of Example 19 in 15 mL of CH2Cl2 was added 1 g of solid NaHCO3 followed by 0.525 g (3.12 mmol) of allyl iodide. The reaction mixture was stirred overnight at room temperature, then filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 0-1% MeOH in CH2Cl2. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo
  3. customThe residue was purified on a silica gel flash chromatography column
  4. washeluted with 0-1% MeOH in CH2Cl2
  5. customEvaporation of the purified fractions
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-fe690e218663451d8bdfe5c33b03175d
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Linked notes

Loading…