Triethylamine → HCID 21544524, compound

HRID 1606777Notes

Reaction equation

HRID 1606777 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](Cl)=[O:8])(=[O:3])[CH3:2].[CH:14]12[O:21][CH:18]([CH2:19][CH2:20]1)[CH2:17][NH:16][CH2:15]2.C(N(CC)CC)C>C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7]([N:16]1[CH2:15][CH:14]2[O:21][CH:18]([CH2:19][CH2:20]2)[CH2:17]1)=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796682-Acetoxybenzoyl chlorideHCID 120692318-Oxa-3-azabicyclo[3.2.1]octane

Product 1

HCID 21544524HCID 21544524, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

o-Acetoxybenzoyl chloride (0.1 mole, 19.85 grams) was slowly added to a mixture of 8-oxa-3-azabicyclo(3.2.1)octane (0.1 mole, 11.13 grams) and triethylamine (0.1 mole) in 60 ml of benzene at 20° C. The reaction mixture was stirred 2.5 hours at 25° C. The salt was filtered off and washed with benzene. After removal of benzene, the product was obtained as a viscous liquid which was purified by column chromatography (alumina). Impurities were eluted with ether and the product with methanol to yield the product represented by formula (IX).

Workup

  1. filtrationThe salt was filtered off
  2. washwashed with benzene
  3. customAfter removal of benzene
  4. customthe product was obtained as a viscous liquid which
  5. customwas purified by column chromatography (alumina)
  6. washImpurities were eluted with ether
  7. customthe product with methanol to yield the product

Sources & evidence

ORD record
ord-ea3165aec90f479499dd948299ec83d1
Source dataset
uspto-grants-1976_04
Patent number
US03953596

Reaction notes

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