Triethylamine → HCID 13189040, compound

HRID 1995309Notes

Reaction equation

HRID 1995309 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[C:15](=[O:17])[O:16][C:5]=2[CH:4]=1.C(N(CC)CC)C.Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:34][CH:33]2[CH2:35][CH2:36][CH:30]1[CH2:31][CH2:32]2>O>[CH:30]12[CH2:36][CH2:35][CH:33]([CH2:32][CH2:31]1)[CH2:34][N:29]2[CH2:28][CH2:27][N:12]1[CH2:13][CH2:14][C:9]2[C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[O:16][C:15](=[O:17])[C:10]=2[CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131369188-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-oneHCID 204881482-(2-Chloroethyl)-2-azabicyclo[2.2.2]octane hydrochloride

Product 1

HCID 13189040HCID 13189040, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared by the method described for Example 27 from 1,2,3,4-tetrahydro-8-methoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one (3.0 g, 0.013 moles), triethylamine (3.9 ml, 0.028 moles), and 2-(2-chloroethyl)-2-azabicyclo[2.2.2]octane hydrochloride (2.9 g, 0.014 moles). Reflux time is 3 weeks. The crude product is dissolved in water, extracted with ethyl acetate, precipitated by the addition of solid potassium carbonate, filtered off, rinsed with water, and dried to yield the final product (2.3 g), mp 112°-113° C.

Workup

  1. customPrepared by the method
  2. temperatureReflux time
  3. waitis 3 weeks
  4. extractionextracted with ethyl acetate
  5. customprecipitated by the addition of solid potassium carbonate
  6. filtrationfiltered off
  7. washrinsed with water
  8. customdried

Sources & evidence

ORD record
ord-156a1649d0e24fc5afb3aaed00bfaa85
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

Loading…