2-(Phenylmethyl)oxirane → HCID 22905182, compound

HRID 865341Notes

Reaction equation

HRID 865341 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) 7.24-7.18 (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-328cf0cb4af0487eb83ff327615eb3df
Source dataset
uspto-grants-1996_10
Patent number
US05565449

Reaction notes

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