Ammonia → HCID 21940701, compound

HRID 2179261Notes

Reaction equation

HRID 2179261 reaction equation
[O-:1]P([O-])([O-])=O.[K+].[K+].[K+].CN[CH2:11][CH2:12][NH:13][CH3:14].I[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][NH2:20].N.[C:25]1([CH3:31])C=CC=CC=1>[Cu]I.O>[NH2:20][CH2:19][C:18]1[CH:17]=[C:16]([N:13]2[CH2:12][CH2:11][CH2:31][CH2:25][C:14]2=[O:1])[CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 1140TolueneHCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 970123-Iodobenzylamine

Product 1

HCID 21940701HCID 21940701, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), 6-valerolactam (120 mg, 1.21 mmol), K3PO4 (430 mg, 2.03 mmol), briefly evacuated and backfilled with argon. N,N′-Dimethylethylenediamine (11 μL, 0.10 mmol, 10 mol %), 3-iodobenzylamine (134 μL, 1.01 mmol), and toluene (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 100° C. for 18 h. The resulting pale yellow suspension was allowed to reach room temperature, and then 30% aq ammonia (1 mL) and water (10 mL) were added. The biphasic mixture was extracted with CH2Cl2 (3×15 mL). The combined organic phases were dried (Na2SO4), concentrated, and the residue was purified by flash chromatography on silica gel (2×15 cm; CH2Cl2 (saturated with 30% aq ammonia)-CH2Cl2—MeOH 10:10:1; 15 mL fractions). Fractions 14-19 provided 199 mg (96% yield) of the product as a pale yellow oil.

Workup

  1. custombriefly evacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. extractionThe biphasic mixture was extracted with CH2Cl2 (3×15 mL)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated
  7. customthe residue was purified by flash chromatography on silica gel (2×15 cm; CH2Cl2 (saturated with 30% aq ammonia)-CH2Cl2—MeOH 10:10:1; 15 mL fractions)

Sources & evidence

ORD record
ord-6fc66676c8ee4b76a2daeb8bd6aa74bb
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

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