Isopropylamine → Methyl 2-(2-hydroxy-3-(isopropylamino)propoxy)benzoate

HRID 1981650Notes

Reaction equation

HRID 1981650 reaction equation
[O:1]1[CH2:15][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH:16]([NH2:19])([CH3:18])[CH3:17]>CO>[OH:1][CH:2]([CH2:15][NH:19][CH:16]([CH3:18])[CH3:17])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 279510Methyl 2-(oxiran-2-ylmethoxy)benzoate

Product 1

HCID 12548683Methyl 2-(2-hydroxy-3-(isopropylamino)propoxy)benzoateYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.1 g (0.01 mole) of methyl 2-(2,3-epoxypropoxy)benzoate, 10 mL of isopropylamine and 10 mL of methanol was heated to reflux for three hours. The reaction medium was then evaporated under reduced pressure to provide the amine as an oil. The oil was treated with hexane:ethyl acetate (9:1) to generate the free amine as a crystalline product in 63% yield: m.p. 78°-79° C. The NMR spectrum and elemental analysis were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for three hours
  3. customThe reaction medium was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-6c7f1647ef7a4808a2bbf9fe5ee1d7ca
Source dataset
uspto-grants-1986_06
Patent number
US04593119

Reaction notes

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