Styrene Oxide → alpha-[[[2-(Phenylmethoxy)propyl]amino]methyl]benzenemethanol

HRID 1681349Notes

Reaction equation

HRID 1681349 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]([O:17][CH:18]([CH3:21])[CH2:19][NH2:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:11]1([CH2:10][O:17][CH:18]([CH3:21])[CH2:19][NH:20][CH2:1][CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[OH:9])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 7276Styrene OxideHCID 2960152-(Benzyloxy)propan-1-amine

Product 1

HCID 19806395alpha-[[[2-(Phenylmethoxy)propyl]amino]methyl]benzenemethanolYield 84.1%

Conditions

Temperature
140 °C

Procedure

A mixture of styrene oxide (1.96 g, 0.010 mol) and 2-benzyloxypropylamine (2.48 g, 0.15 mol) was heated at 140° C. for 6 hours and then allowed to cool to ambient temperature and stand for 12 hours. The solidified reaction mixture was triturated with isooctane and filtered to obtain an impure solid that was recrystallized from isooctane to obtain 2.40 g of a white solid (84% yield); mp 90°-100° C. (undefined).

Workup

  1. temperatureto cool to ambient temperature
  2. customThe solidified reaction mixture
  3. customwas triturated with isooctane
  4. filtrationfiltered
  5. customto obtain an impure solid
  6. customthat was recrystallized from isooctane

Sources & evidence

ORD record
ord-9930972b977f40ce97126d92214321de
Source dataset
uspto-grants-1992_12
Patent number
US05171753

Reaction notes

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