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

HRID 1287490Notes

Reaction equation

HRID 1287490 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.Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(CC)CC)C>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3[CH2:14][CH2:13][N:12]([CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH2:11][C:10]=3[C:15](=[O:17])[O:16][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 131369188-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

Product 1

HCID 144503251,2,3,4-Tetrahydro-8-methoxy-3-(2-morpholinoethyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10 g (0.043 m) of 1,2,3,4-tetrahydro-8-methoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one, 11.2 g (0.06 m) of N-(2-chloroethyl)morpholine HCl and 14.2 g of triethylamine (0.14 m) in 170 ml of abs. EtOH was refluxed with stirring and protection from moisture for 4 hours. The reaction was filtered hot, cooled slightly and treated with dry HCl. The resulting precipitate was filtered and washed with EtOH, then ether; yield 14.6 g (81%). Crystallization from methanol afforded analytical material, mp 237°-40°C.

Workup

  1. filtrationThe reaction was filtered hot
  2. temperaturecooled slightly
  3. additiontreated with dry HCl
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with EtOH
  6. customCrystallization from methanol afforded analytical material, mp 237°-40°C.

Sources & evidence

ORD record
ord-1b7bb29ccf5848b4b8660a211add5e95
Source dataset
uspto-grants-1976_10
Patent number
US03984546

Reaction notes

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