Sodium Hydroxide → HCID 21544532, compound

HRID 1606776Notes

Reaction equation

HRID 1606776 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.Cl.[CH:12]12[O:19][CH:16]([CH2:17][CH2:18]1)[CH2:15][NH:14][CH2:13]2.[OH-].[Na+]>O>[C:2]([N:14]1[CH2:13][CH:12]2[O:19][CH:16]([CH2:17][CH2:18]2)[CH2:15]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)2×HCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochloride

Product 1

HCID 21544532HCID 21544532, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Nicotinoyl chloride hydrochloride (17.81 grams, 0.1 mole) was slowly added to a mixture of 8-oxa-3-azabicyclo(3.2.1) octane hydrochloride (15 grams, 0.1 mole) and sodium hydroxide (15 grams) in 300 ml of water, at 10° C. After the addition of nicotinoyl chloride hydrochloride, the reaction mixture was stirred for 2 hours and then left overnight at room temperature. The product was extracted from the reaction mixture with diethyl ether and the extract treated with DARCO G60 (activated carbon). After the removal of ether, the product was obtained as a clear liquid (10 grams, 46% yield) which crystallized. The product 3-nicotinoyl-8-oxa-3-azabicyclo(3.2.1)octane was recrystallized from a blend of about 30% petroleum ether (boiling point 30°-60° C.) and 70% diethyl ether (v/v) to white crystals having a melting point of 48°-49.5° C.

Workup

  1. waitleft overnight at room temperature
  2. extractionThe product was extracted from the reaction mixture with diethyl ether
  3. additionthe extract treated with DARCO G60 (activated carbon)
  4. customAfter the removal of ether

Sources & evidence

ORD record
ord-c408661161ad4d59ad5aabeb1ed3c0ef
Source dataset
uspto-grants-1976_04
Patent number
US03953596

Reaction notes

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