Acetonitrile → HCID 19028147, compound

HRID 264997Notes

Reaction equation

HRID 264997 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:15][CH3:16])[O:7][CH2:6]1)[CH:2]=[CH2:3].[CH2:17](I)[CH2:18][CH3:19].C([O-])([O-])=O.[K+].[K+].C(#N)C>CCOCC>[CH2:1]([N:4]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:15][CH3:16])[O:7][CH2:6]1)[CH2:17][CH2:18][CH3:19])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 141036023-(N-Allylamino)-5-methoxychroman

Product 1

HCID 19028147HCID 19028147, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
47 °C

Procedure

3-(N-Allylamino)-5-methoxychroman (1.3 g, 5.9 mmol) prepared analogous to example 26, n-propyl iodide (2.1 mL, 21 mmol), anhyrous K2CO3 (3.0 g, 21 mmol) and acetonitrile (5.5 mL) were stirred under N2 at 47° C. (oilbath temp) for five days until GC indicated complete reaction. Ether (40 mL) was added, the salts were filtered off by suction and the clear filtrate was concentrated in vacuo to afford 3-(N-allyl-N-n-propylamino)-5-methoxy chroman (1.24 g, 81% yield) as an oil. The base was precipitated from an ether solution by adding a slight excess of HCl (approx. 3M in ether). Crystallization of the crude HCl salt afforded colourless needles. Mp 117°-118° C.

Workup

  1. customreaction
  2. filtrationthe salts were filtered off by suction
  3. concentrationthe clear filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a3f9d334ca594e178ea77940ed17c684
Source dataset
uspto-grants-1997_07
Patent number
US05646309

Reaction notes

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