Tert-Butylamine → HCID 559935, compound

HRID 1981648Notes

Reaction equation

HRID 1981648 reaction equation
[O:1]1[CH2:15][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17]>CO>[OH:1][CH:2]([CH2:15][NH:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 2771933methyl 4-(oxiran-2-ylmethoxy)benzoate

Product 1

HCID 559935HCID 559935, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-(2,3-epoxypropoxy)benzoate (prepared as described in Example I) (2.1 g, 0.01 mole), 10 mL of t-butylamine 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 free amine was crystallized from hexane-ethyl acetate in 65% yield: m.p. 88°-89° 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-e9d009c679734c63859ec5c5cc5985b2
Source dataset
uspto-grants-1986_06
Patent number
US04593119

Reaction notes

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