Phenylacetyl chloride → HCID 21544543, compound

HRID 1606774Notes

Reaction equation

HRID 1606774 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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:1]1([CH2:7][C:8]([N:14]2[CH2:13][CH:12]3[O:19][CH:16]([CH2:17][CH2:18]3)[CH2:15]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chloride2×HCID 14798Sodium HydroxideHCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochloride

Product 1

HCID 21544543HCID 21544543, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phenylacetyl chloride (15.46 grams, 0.1 mole) (Aldrich Chemical Co., Inc., Milwaukee, Wisconsin) 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 phenylacetyl chloride, the reaction mixture was stirred at room temperature for 2 hours. The crystalline solid (22.1 grams, 95.6%) which separated was filtered off, washed with water, and finally recrystallized from a blend of about 30% petroleum ether (boiling point 30°-60° C.) and 70% diethyl ether (v/v) to yield the product 3-phenylacetyl-8-oxa-3-azabicyclo(3.2.1)octane which had a melting point of 106°-106.5° C.

Workup

  1. customThe crystalline solid (22.1 grams, 95.6%) which separated
  2. filtrationwas filtered off
  3. washwashed with water
  4. customfinally recrystallized from a blend of about 30% petroleum ether (boiling point 30°-60° C.) and 70% diethyl ether (v/v)

Sources & evidence

ORD record
ord-9e452587f36c4ec28ab9c6e1eca18474
Source dataset
uspto-grants-1976_04
Patent number
US03953596

Reaction notes

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