Styrene Oxide → 2-allylamino-1-phenyl-ethanol

HRID 1639157Notes

Reaction equation

HRID 1639157 reaction equation
[CH2:1]1[O:9][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([NH2:13])[CH:11]=[CH2:12]>>[CH2:10]([NH:13][CH2:1][CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[OH:9])[CH:11]=[CH2:12]

Participants

3

Reactant 2

HCID 7276Styrene OxideHCID 7853Allylamine

Product 1

HCID 2925542-allylamino-1-phenyl-ethanol

Procedure

A mixture of styrene oxide (24 mL, 0.2 moles) and allylamine (60.8 mL, 0.8 moles) was heated to reflux under nitrogen atmosphere, for 24 hours. Upon cooling, product crystallized and was triturated with hexane. Recrystallization from hexane afforded the title compound essentially uncontaminated by the other possible regioisomer. Ms m+/z=177; H1NMR (CDCl3): δ 7.3 (br.s, 5H), 5.6-6.1 (m, 1H), 4.9-5.4 (m, 2H), 4.75 (m, 1H), 3.2 (br.d, 2H), 2.9 (br.s, 2H), 2.7 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen atmosphere, for 24 hours
  3. temperatureUpon cooling
  4. customproduct crystallized
  5. customwas triturated with hexane
  6. customRecrystallization from hexane

Sources & evidence

ORD record
ord-cc843f7929f04dc0a82af1ef5073e075
Source dataset
uspto-grants-1989_11
Patent number
US04882429

Reaction notes

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