Acetonitrile → HCID 19028147, compound

HRID 2257348Notes

Reaction equation

HRID 2257348 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-0c690f19277f4f88a2e91c6c5d27b8ad
Source dataset
uspto-grants-1997_08
Patent number
US05656658

Reaction notes

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