Diallylamine → Ammonia methanol

HRID 1750547Notes

Reaction equation

HRID 1750547 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][CH:11]2[CH2:16][CH:15]3[CH:13]([O:14]3)[CH2:12]2)=[CH:5][CH:4]=1.[CH2:17]([NH:20][CH2:21][CH:22]=[CH2:23])[CH:18]=[CH2:19]>C(O)C>[NH3:20].[CH3:1][OH:2].[CH2:17]([N:20]([CH2:21][CH:22]=[CH2:23])[CH:13]1[CH2:12][CH:11]([O:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:16][CH:15]1[OH:14])[CH:18]=[CH2:19]

Participants

5

Reactant 2

HCID 31279DiallylamineHCID 118024581HCID 118024581, compound

Product 2

HCID 21705897Ammonia methanolYield 0.1%HCID 118034887HCID 118034887, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 3[(4-methoxyphenyl)methoxy]-6-oxabicyclo[3.1.0]hexane (10.21 g, 46.4 mmol) in ethanol (66 ml) was added bis(prop-2-en-1-yl)amine (CAS number 124-02-7; 13.51 g, 139 mmol). The reaction was heated in a sealed vial at 105° C. for 72 hours. The reaction mixture was concentrated in vacuo then purified by column chromatography (silica, 0-50% ethyl acetate/petrol then 0-30% (0.1% ammonia/methanol)/ethyl acetate) to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthen purified by column chromatography (silica, 0-50% ethyl acetate/petrol

Sources & evidence

ORD record
ord-17d7d62c534f4edfbe0e94d5a45aa3be
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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