Iodoethanol → HCID 12345988, compound

HRID 1053561Notes

Reaction equation

HRID 1053561 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2].I[CH2:12][CH2:13][OH:14].C(N(C(C)C)CC)(C)C>C(#N)C>[CH:1]([N:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:12][CH2:13][OH:14])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 12225IodoethanolHCID 13032N-IsopropylanilineHCID 81531Diisopropylethylamine

Product 1

HCID 12345988HCID 12345988, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 4a (617 mg, 4.6 mmol) was reacted with 2-Iodoethanol (0.54 mls, 6.9 mmol) and diisopropylethylamine (1.2 mls, 6.9 mmol) in ACN (20 mls) at 30° C. for 48 hours. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane and EtOAc to provide the intermediate 4b (483 mg, 2.7 mmol, 59% yield) as a light brown oil. HRMS (ESI, positive) m/z calcd. for C11H18N1O1 [M+H]+: 180.13829, found: 180.13829. 1H NMR (400 MHz, CDCl3) δ 7.28-7.19 (t, J=8.0 Hz, 2H), 6.92-6.85 (d, J=8.2 Hz, 2H), 6.83-6.75 (t, J=7.3 Hz, 1H), 4.03-3.88 (hept, J=6.6 Hz, 1H), 3.70-3.62 (t, J=6.2 Hz, 2H), 3.34-3.24 (m, 2H), 1.19-1.12 (d, J=6.6 Hz, 6H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography with hexane and EtOAc

Sources & evidence

ORD record
ord-06a7e9b19a5a4a86936d8e877b88e99b
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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