Triethylamine → 1,2,3,4-Tetrahydro-8,9-dimethoxy-3-(2-morpholinoethyl)5H-[1]benzopyrano-[3,4-c]pyridin-5-one

HRID 597249Notes

Reaction equation

HRID 597249 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[C:11]3[CH2:16][CH2:15][NH:14][CH2:13][C:12]=3[C:17](=[O:19])[O:18][C:5]=2[CH:4]=1.Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(N(CC)CC)C>C(O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[C:11]3[CH2:16][CH2:15][N:14]([CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH2:13][C:12]=3[C:17](=[O:19])[O:18][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 108252898,9-dimethoxy-1,2,3,4-tetrahydro-5H-chromeno[3,4-c]pyridin-5-one

Product 1

HCID 214471711,2,3,4-Tetrahydro-8,9-dimethoxy-3-(2-morpholinoethyl)5H-[1]benzopyrano-[3,4-c]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7.85 g (0.03 m) of 1,2,3,4-tetrahydro-8,9-dimethoxy-5H-[1]benzopyrano [3,4-c]pyridin-5-one, 6.15 g (0.033 m) of N-(2-chloroethyl) morpholine HCl and 7.08 g (0.07 m) of triethylamine in 250 cc of ethanol was refluxed for a hr. and filtered hot. Treatment of the hot reaction solution with excess HCl 6 hr. and cooling to room temperature afforded crude product. Crystallization from 75% EtOH afforded analytical material mp. 238°-40° C.

Workup

  1. temperaturewas refluxed for a hr
  2. filtrationand filtered hot
  3. customwith excess HCl 6 hr
  4. customafforded crude product
  5. customCrystallization from 75% EtOH afforded analytical material mp. 238°-40° C.

Sources & evidence

ORD record
ord-8f1a89746edc4db29f4f8f5f6bfa5305
Source dataset
uspto-grants-1977_03
Patent number
US04013671

Reaction notes

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