Sodium Iodide → HCID 86625664, compound

HRID 68199Notes

Reaction equation

HRID 68199 reaction equation
[C:1]([N:5]([CH:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:18]([CH3:20])[CH3:19])[O:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[I-:27].[Na+]>CC(C)=O>[C:1]([N:5]([CH:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:18]([CH3:20])[CH3:19])[O:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][I:27])=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 22733773N-tert-Butyl-N-{1-[4-(chloromethyl)phenyl]ethoxy}-2-methyl-1-phenylpropan-1-amine

Product 1

HCID 86625664HCID 86625664, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 50-mL round-bottom flask equipped with a magnetic stirbar was added chloromethyl alkoxyamine 3 (1.789 g, 4.784 mmol) and acetone (20 mL). To the resulting solution was added sodium iodide (2.869 g, 19.14 mmol, 4 equiv) and the reaction mixture was capped with a rubber septum and allowed to stir for 24 hours at room temperature. The sodium chloride side product was remove by gravity filtration, and the filtrate was concentrated on a rotary evaporator. The crude oily product was purified by flash chromatography, eluting with hexanes. The desired iodomethyl akoxyamine 4 was obtained as a colorless oil (1.968 g, 88.3% yield). ESI-MS: m/z=466.0, observed; 465.41, calculated. 1H NMR (500 MHz, CDCl3, both diastereomers) δ 7.5-7.1 (m, 18H), 5.35 (t, 2H) 4.90 (q+q, 2H, both diastereomers), 4.55 (s, 4H), 3.55 (m, 2H), 3.40 (d, 1H, minor diastereomer), 3.30 (d, 1H, major diastereomer), 2.40 (m, 2H, both diastereomer), 2.30 (d, 2H), 1.65 (d, 3H, minor diastereomer), 1.58 (d, 3H, major diastereomer), 1.33 (d, 3H, minor diastereomer), 1.05 (s, 9H, major diastereomer), 0.98 (s, 6H), 0.95 (d, 3H, major diastereomer), 0.89 (d, 12H), 0.85 (d, 6H), 0.82 (s, 9H, minor diastereomer), 0.68 (s, 2H), 0.59 (d, 3H, minor diastereomer), 0.28 (d, 3H, major diastereomer).

Workup

  1. customTo a 50-mL round-bottom flask equipped with a magnetic stirbar
  2. customthe reaction mixture was capped with a rubber septum
  3. customThe sodium chloride side product was remove by gravity filtration
  4. concentrationthe filtrate was concentrated on a rotary evaporator
  5. customThe crude oily product was purified by flash chromatography
  6. washeluting with hexanes

Sources & evidence

ORD record
ord-0a286e3ff5b548f5ad46e9563e234492
Source dataset
uspto-grants-2014_09
Patent number
US08821922B2

Reaction notes

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