Benzamide → HCID 86609296, compound

HRID 2179243Notes

Reaction equation

HRID 2179243 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C)[C@@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1N.I/C=C/CCCC>[Cu]I.C1(C)C=CC=CC=1>[CH:25]([C:2]1([CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1)[C:1]([NH2:9])=[O:8])=[CH:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 2331BenzamideHCID 62657Potassium Phosphate, TribasicHCID 5362933(1E)-1-Iodo-1-hexeneHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamine

Product 1

HCID 86609296HCID 86609296, compoundYield 668.6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
25 °C

Procedure

A 15 mL resealable Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 mol %), benzamide (145 mg, 1.20 mmol), K3PO4 (430 mg, 2.03 mmol), evacuated and backfilled with argon. trans-N,N-Dimethyl-1,2-cyclohexanediamine (16 μL, 0.102 mmol, 10 mol %), trans-1-iodo-1-hexene (143 μL, 1.00 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 25° C. for 24 h. The resulting light blue suspension was allowed to reach room temperature and then filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated, the residue was dissolved in 5 mL of dichloromethane and purified by flash chromatography on silica gel (2×15 cm, hexane-ethyl acetate, 15 mL fractions). Fractions 12-19 provided 140 mg (69% yield) of the desired product as white needles.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe residue was dissolved in 5 mL of dichloromethane
  7. custompurified by flash chromatography on silica gel (2×15 cm, hexane-ethyl acetate, 15 mL fractions)

Sources & evidence

ORD record
ord-02d73fd03eea4b25848b8f5275298220
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

Loading…