Isopropylamine → 1-{4-[2-(Allyloxy)-ethyl]phenoxy}-3-isopropylamino propan-2-ol

HRID 1765492Notes

Reaction equation

HRID 1765492 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:17]=[CH:16][C:10]([O:11][CH2:12][CH:13]2[CH2:15][O:14]2)=[CH:9][CH:8]=1)[CH:2]=[CH2:3].[CH:18]([NH2:21])([CH3:20])[CH3:19]>CO>[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:17]=[CH:16][C:10]([O:11][CH2:12][CH:13]([OH:14])[CH2:15][NH:21][CH:18]([CH3:20])[CH3:19])=[CH:9][CH:8]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 167262652-[4-(2-Allyloxy-ethyl)-phenoxymethyl]-oxirane

Product 1

HCID 116593381-{4-[2-(Allyloxy)-ethyl]phenoxy}-3-isopropylamino propan-2-olYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the compound of formula (5) (3.70 g, 0.016 mol), isopropyl amine (7.46 ml, 0.127 mol) in methanol (20 ml) was stirred under reflux for 2 hours and then concentrated. The residue was partitioned between chloroform and water. The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. The residue was crystallized from pet ether to afford compound of formula (1) as a white solid 3.47 g (75%) mp 52–53° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationconcentrated
  3. customThe residue was partitioned between chloroform and water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was crystallized from pet ether

Sources & evidence

ORD record
ord-2f976705f55d4c7eb0570c4bdabb6027
Source dataset
uspto-grants-2007_06
Patent number
US07227039B2

Reaction notes

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