N'-Hydroxybenzenecarboximidamide → HCID 67300490, compound

HRID 2047640Notes

Reaction equation

HRID 2047640 reaction equation
[C:1](=[N:9][OH:10])([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[O:17]=[C:18]1[CH2:23][CH:22]([C:24](OC)=O)[CH2:21][CH2:20][NH:19]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:2]1([C:1]2[N:8]=[C:24]([CH:22]3[CH2:21][CH2:20][NH:19][C:18](=[O:17])[CH2:23]3)[O:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 69186N'-HydroxybenzenecarboximidamideHCID 516892Sodium BicarbonateHCID 23093678Methyl 2-oxopiperidine-4-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67300490HCID 67300490, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add benzamidoxime (5.63 g, 41.36 mmol) to a 1M solution of potassium t-butoxide (31 mL, 31 mmol) in tetrahydrofuran and anhydrous tetrahydrofuran (442 mL). Add methyl 2-oxopiperidine-4-carboxylate (5 g, 31.8 mmol) and stir overnight at room temperature. Pour reaction over saturated aqueous sodium bicarbonate and extract into chloroform. Separate layers and extract the aqueous phase with additional chloroform. Dry the combined organic layers over anhydrous magnesium sulfate, filter, and concentrate to dryness under reduced pressure. Purify the resulting residue by flash chromatography (silica gel), eluting with 1-5% 7 N ammoniated methanol in dichloromethane to afford the title compound (4.15 g). 1H NMR (CDCl3) δ 2.19 (m, 1H), 2.34 (m, 1H), 2.8-2.95 (m, 2H), 3.44-3.52 (m, 2H), 3.57 (m, 1H), 6.13 (bs, 1H), 7.45-7.54 (m, 3H), 8.0-8.11 (m, 2H).

Workup

  1. additionPour
  2. extractionextract into chloroform
  3. extractionSeparate layers and extract the aqueous phase with additional chloroform
  4. dry with materialDry the combined organic layers over anhydrous magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate to dryness under reduced pressure
  7. customPurify the resulting residue by flash chromatography (silica gel)
  8. washeluting with 1-5% 7 N ammoniated methanol in dichloromethane

Sources & evidence

ORD record
ord-79b38f5ab4bb4213ba202d4f038bd7da
Source dataset
uspto-grants-2013_11
Patent number
US08592590B2

Reaction notes

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