Triethylamine → 3-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8,9-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 1995297Notes

Reaction equation

HRID 1995297 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]2[C:9]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[C:15](=[O:17])[O:16][C:4]=2[CH:3]=1.C(N(CC)CC)C.Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:35][CH:34]2[CH2:36][CH2:37][CH:31]([CH2:32][CH2:33]2)[CH2:30]1>C(O)C>[CH:34]12[CH2:36][CH2:37][CH:31]([CH2:32][CH2:33]1)[CH2:30][N:29]([CH2:28][CH2:27][N:12]1[CH2:13][CH2:14][C:9]3[C:5]4[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=4[O:16][C:15](=[O:17])[C:10]=3[CH2:11]1)[CH2:35]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126123263-(2-Chloroethyl)-3-azabicyclo[3.2.2]nonane--hydrogen chloride (1/1)HCID 131369151,2,3,4-Tetrahydro-8,9-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one

Product 1

HCID 131890273-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8,9-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-oneYield 46.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-8,9-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one (6.0 g, 0.026 moles), triethylamine (6.1 g, 0.060 moles), and 3-(2-chloroethyl)-3-azabicyclo[3.2.2]nonane hydrochloride (6.3 g, 0.028 moles) in absolute ethanol (150 ml) is stirred at reflux under a nitrogen atmosphere for 24 hours. The crude product precipitates as the free base as the reaction mixture is cooled slowly to room temperature. The product is filtered and recrystallized from absolute ethanol to yield the final product (4.6 g), mp 174°-175° C.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 24 hours
  2. customThe crude product precipitates as the free base as the reaction mixture
  3. filtrationThe product is filtered
  4. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-1c666ea6c3df4477bed4b05e535f9db0
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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