2-(Phenylmethyl)oxirane → HCID 22905182, compound

HRID 1653872Notes

Reaction equation

HRID 1653872 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, 0.186mol) in methanol was added to a methanolic solution of 3-phenylpropyleneoxide (5.07 grams, 0.037mol) 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, NCH2CH=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-cfb57e491c4d41cf9eb09186020a6224
Source dataset
uspto-grants-1995_04
Patent number
US05403836

Reaction notes

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