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

HRID 2166520Notes

Reaction equation

HRID 2166520 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 pessure 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 pessure

Sources & evidence

ORD record
ord-42dca44b243341ca959e9fdbe95a18c8
Source dataset
uspto-grants-1983_06
Patent number
US04387103

Reaction notes

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