Sodium Hydroxide → 1-(8-Oxa-3-azabicyclo[3.2.1]oct-3-yl)-1-heptanone

HRID 1606775Notes

Reaction equation

HRID 1606775 reaction equation
[C:1](Cl)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl.[CH:11]12[O:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][NH:13][CH2:12]2.[OH-].[Na+]>O>[C:1]([N:13]1[CH2:12][CH:11]2[O:18][CH:15]([CH2:16][CH2:17]2)[CH2:14]1)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 17313Heptanoyl chloride2×HCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochloride

Product 1

HCID 215445421-(8-Oxa-3-azabicyclo[3.2.1]oct-3-yl)-1-heptanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Heptanoyl chloride (14.86 grams, 0.1 mole) was slowly added to a mixture of 8-oxa-3-azabicyclo(3.2.1)octane hydrochloride product of Example 3 (14.96 grams, 0.1 mole) and sodium hydroxide (10 grams) in 300 ml water, at 10° C. After the addition of heptanoyl chloride, 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 treated with DARCO G60 (activated carbon) After the removal of the diethyl ether, the product 3-heptanoyl-8-oxa-3-azabicyclo (3.2.1)octane was obtained as a clear liquid.

Workup

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

Sources & evidence

ORD record
ord-38eddb3b33824f37b602832f4aac9436
Source dataset
uspto-grants-1976_04
Patent number
US03953596

Reaction notes

Loading…