Isobutyl iodide → HCID 86646578, compound

HRID 2080548Notes

Reaction equation

HRID 2080548 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.I[CH2:14][CH:15]([CH3:17])[CH3:16].C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 81531DiisopropylethylamineHCID 153902972-[(6-Chloro-pyridin-3-ylmethyl)-amino]-ethanol

Product 1

HCID 86646578HCID 86646578, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 2.0 grams (0.007 mole) of 2-{[(6-chloro(3-pyridyl))methyl]amino}ethan-1-ol (known compound), 1.29 gram (0.007 mole) of 1-iodo-2-methylpropane and 0.9 gram (0.007 mole) if diisopropylethylamine in 50 mL of acetonitrile was heated at reflux for 16 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, eluting with a mixture of diethyl ether and hexanes. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.37 grams of 2-{[(6-chloro(3-pyridyl))methyl](2-methylpropyl)amino}ethan-1-ol. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with a mixture of diethyl ether and hexanes
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a2ff2b2c2c24d668e08418d4cd2cf4d
Source dataset
uspto-grants-2011_04
Patent number
US07932393B2

Reaction notes

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