Triethylamine → HCID 2788659, compound

HRID 2061451Notes

Reaction equation

HRID 2061451 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:19](Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>C(OCC)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 891481,4-Benzodioxan-6-ylamine

Product 1

HCID 2788659HCID 2788659, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 22.5 g (149 mmol) 2,3-dihydro-benzo[1,4]dioxin-6-ylamine and 25 ml (179 mmol) triethylamine in 1 l diethyl ether is added at 12° C. within 10 minutes 20 ml (164 mmol) pivaloyl chloride dissolved in 250 ml diethyl ether. The temperature is kept between 12-16° C. The reaction mixture is stirred at room temperature for 1 hour. Then it is washed with 2× with 300 ml water, 2× with 150 ml 1N HCl and 2× with brine, dried with Na2SO4 and partially evaporated to a volume of 80 ml. This leads to a suspension. Hexane is added and the solid is filtered to give N-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2,2-dimethyl-propionamide.

Workup

  1. customis kept between 12-16° C
  2. washThen it is washed with 2× with 300 ml water, 2× with 150 ml 1N HCl and 2× with brine
  3. dry with materialdried with Na2SO4
  4. custompartially evaporated to a volume of 80 ml
  5. additionHexane is added
  6. filtrationthe solid is filtered

Sources & evidence

ORD record
ord-8dd84c5ca0bf411ab8df9998d6b514d3
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

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