18-Crown-6 → HCID 22914705, compound

HRID 1377695Notes

Reaction equation

HRID 1377695 reaction equation
Cl[N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][O:10][C:9]2=[O:18])[CH2:4][CH2:3]1.O=O.[K+].C1OCCOCCOCCOCCOCCOC1.C[Si]([C:44]#[N:45])(C)C>CCOCC>[C:44]([CH:3]1[CH2:4][CH:5]([N:8]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][O:10][C:9]2=[O:18])[CH2:6][CH2:7][NH:2]1)#[N:45]

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 6154112030-88-52×HCID 82115Trimethylsilyl cyanideHCID 22914719HCID 22914719, compound

Product 1

HCID 22914705HCID 22914705, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

1-(N-chloro-4-piperidyl)-3,1-benzoxazin-2-one from Step 1 above (230 mg, 0.86 mmol) was dissolved in warm ether (30 mL) and the solution was added dropwise to a suspension of potassium superoxide (135 mg, 1.9 mmol) and 18-crown-6 (10 mg, 0.04 mmol) in ether (10 mL). The mixture was stirred at ambient temperature for five days, with two additional lots of 135 mg each of potassium superoxide being added on the second and third days. The reaction was filtered and the filtrate was added dropwise to an ether solution of trimethylsilylcyanide (0.172 mL, 128 mg, 1.3 mmol). The mixture was stirred at ambient temperature for 18 hours, then evaporated to dryness in vacuo. The residue was chromatographed on silica gel eluted with 4:96 MeOH:CH2Cl2. The combined product fractions were evaporated to dryness in vacuo, and the residue was evaporated twice from ether to give 1-(2-cyano-4-piperidyl)-3,1-benzoxazin-2-one: MS (FAB): M+H @ m/e=258.

Workup

  1. additionadded on the second and third days
  2. filtrationThe reaction was filtered
  3. customevaporated to dryness in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluted with 4:96 MeOH
  6. customThe combined product fractions were evaporated to dryness in vacuo
  7. customthe residue was evaporated twice from ether

Sources & evidence

ORD record
ord-b823d9e0bf9e4d55b57697b863e30a19
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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