Ethylamine → HCID 46870291, compound

HRID 1886905Notes

Reaction equation

HRID 1886905 reaction equation
[CH2:1]([N:4]1[C:18](=[O:19])[C:17]2[C:11]3([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:10][C:9]3[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=3[C:7]=2[N:6]=[C:5]1S(C)(=O)=O)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[CH2:34]([NH2:36])[CH3:35].O1CCCC1>C(OCC)C.CN(C)C=O>[CH2:1]([N:4]1[C:18](=[O:19])[C:17]2[C:11]3([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:10][C:9]3[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=3[C:7]=2[N:6]=[C:5]1[NH:36][CH2:34][CH3:35])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 6341Ethylamine2×HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 59637156HCID 59637156, compound

Product 1

HCID 46870291HCID 46870291, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

3-Allyl-2-(methylsulfonyl)-3H-spiro[benzo[h]quinazoline-5,1′-cyclohexan]-4(6H)-one (6, 306 mg, 0.796 mmol) and potassium carbonate (165 mg, 1.19 mmol) were added to 1 mL of dry dimethylformamide stirring under nitrogen atmosphere. A 2.0M solution of ethylamine in tetrahydrofuran (1 mL, 2 mmol) was then added, and the reaction was tightly capped and allowed to stir at room temperature for 5 hours. Another 1 mL portion of ethylamine solution was added at 5 hours, and the reaction allowed to stir for another 12 hours. At this point, the reaction mixture was diluted with diethyl ether and washed twice with water and once with brine. The organic layer was dried over MgSO4, vacuum filtered, and concentrated in vacuo. The residue was then loaded onto a silica flash column (50 g column, 10% to 33% ethyl acetate:hexanes), which isolated title compound in 85% yield (237 mg, 0.678 mmol) as a white crystalline solid. 1H NMR (500 MHz, CDCl3) δ ppm: 8.15, 7.33, 7.22, 5.94, 5.35, 5.31, 3.60, 3.04, 2.61, 1.72, 1.58, 1.39, 1.30.

Workup

  1. customthe reaction was tightly capped
  2. stirringto stir for another 12 hours
  3. washwashed twice with water and once with brine
  4. dry with materialThe organic layer was dried over MgSO4, vacuum
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2828ba4e6320479f8a429986755e8d6f
Source dataset
uspto-grants-2013_08
Patent number
US08501722B2

Reaction notes

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