2-(Phenylmethyl)oxirane → HCID 22905182, compound

HRID 1488698Notes

Reaction equation

HRID 1488698 reaction equation
[NH2:1][CH:2]=[CH:3][CH3:4].[C:5]1([CH2:11][CH:12]2[O:14][CH2:13]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[CH2:2]([NH:1][CH2:13][CH:12]([OH:14])[CH2:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 948262-(Phenylmethyl)oxiraneHCID 53650673Prop-1-en-1-amine

Product 1

HCID 22905182HCID 22905182, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-aminopropylene (10.6 grams, 0.186 mol) in methanol was added to a methanolic solution of 3-phenylpropyleneoxide (5.07 grams, 0.037 mol) and the mixture heated to reflux for 30 minutes. The mixture was allowed to warm to room temperature and concentrated in vacuo to yield 7.2 grams (99%) of N-allyl-3-phenyl-2-hydroxypropylamine. 1H NMR (CDCl3, dTMS) 7.34-7.18 (5H, m, Ar-H), 5.84 (1H, ddt, 3JHH =17.1 Hz, 3JHH =10.2 Hz, 3JHH =6 Hz, CH2CH), 5.2-5.0 (2H, m, CH=CH2), 3.86 (1H, m, CHOH), 3.19 (2H, m, NCH2 CH=CH2), 2.76-2.66 (3H, m, NCH2CH(OH)(CHHPh), 2.50 (1H, dd 2JHH =12 Hz, 3JHH =9 Hz). 13C NMR (CDCl3) 138.4, 136.5, 129.3, 128.4, 126.3, 116.0, 70.6, 54.0, 51.9, 41.7.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 30 minutes
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7b8db546fce4beeb1ea78e6283daa30
Source dataset
uspto-grants-1997_10
Patent number
US05674863

Reaction notes

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