Potassium Hydroxide → HCID 22141145, compound

HRID 1826438Notes

Reaction equation

HRID 1826438 reaction equation
[OH-].[K+].[CH2:3]([N:9]1[CH2:14][CH:13]2[CH:11]([C:12]2([C:16]2[CH:17]=[CH:18][C:19]([N+:26]([O-:28])=[O:27])=[C:20]([NH:22]C(=O)C)[CH:21]=2)[CH3:15])[CH2:10]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>CO.O>[CH2:3]([N:9]1[CH2:14][CH:13]2[CH:11]([C:12]2([C:16]2[CH:17]=[CH:18][C:19]([N+:26]([O-:28])=[O:27])=[C:20]([NH2:22])[CH:21]=2)[CH3:15])[CH2:10]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22141125HCID 22141125, compound

Product 1

HCID 22141145HCID 22141145, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of potassium hydroxide (100 mg, 1.79 mmol) in methanol (5.0 ml) and water 2.0 ml) was added N-[5-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)-2-nitrophenyl]acetamide (Preparation 46, 534 mg, 1.49 mmol) in methanol (5 ml). The mixture was heated under reflux for 30 minutes and then was allowed to cool. The solvent was removed in vacuo, water (5 ml) was added and the aqueous solution was extracted with ethyl acetate (3×5 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound (360 mg, 76%) as a crude oil which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureto cool
  4. customThe solvent was removed in vacuo, water (5 ml)
  5. additionwas added
  6. extractionthe aqueous solution was extracted with ethyl acetate (3×5 ml)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d07195d401ef4dd988e08456b1424510
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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