1-Pentanol → 6,8-Diazabicyclo[3.2.2]nonane-7,9-dione

HRID 1650174Notes

Reaction equation

HRID 1650174 reaction equation
Cl.Cl.[NH2:3][CH:4]([CH2:9][CH2:10][CH2:11][CH:12]([NH2:17])[C:13](OC)=[O:14])[C:5](OC)=[O:6].C(O)CCCC>C(N(CC)CC)C>[CH:12]12[NH:17][C:5](=[O:6])[CH:4]([NH:3][C:13]1=[O:14])[CH2:9][CH2:10][CH2:11]2

Participants

4

Reactant 2

HCID 62761-PentanolHCID 12853597HCID 12853597, compound

Product 1

HCID 128535996,8-Diazabicyclo[3.2.2]nonane-7,9-dioneYield 69.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 39.0 g (0.134M) of 2,6-diaminoheptanedioic acid, dimethyl ester, dihydrochloride, 56 ml (0.4M) of triethylamine, and 3 L of 1-pentanol was heated under reflux for 4 days. The solution was evaporated to dryness and the residue was recrystallized from chloroform to give 14.3 g of the title compound, mp 280°-3° (69%).

Workup

  1. temperatureunder reflux for 4 days
  2. customThe solution was evaporated to dryness
  3. customthe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-fe3f68aadb2e4a8887aca584be4bd5b5
Source dataset
uspto-grants-1990_05
Patent number
US04923879

Reaction notes

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