Ammonia → HCID 21940701, compound

HRID 1883429Notes

Reaction equation

HRID 1883429 reaction equation
[C:1]1(=[O:7])[NH:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.I[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH2:27].N>[Cu]I.O.C1(C)C=CC=CC=1>[NH2:27][CH2:26][C:25]1[CH:24]=[C:23]([N:6]2[CH2:5][CH2:4][CH2:3][CH2:2][C:1]2=[O:7])[CH:30]=[CH:29][CH:28]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 126652-PiperidoneHCID 62657Potassium Phosphate, TribasicHCID 970123-Iodobenzylamine

Product 1

HCID 21940701HCID 21940701, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), δ-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-cdcc4e2d70d0452098bbba8d2c8eb183
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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