Pyridine → HCID 14666700, compound

HRID 477946Notes

Reaction equation

HRID 477946 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6](=[O:16])[N:7]2[C:12]=1[C:11]1[S:13][CH:14]=[CH:15][C:10]=1[CH2:9][CH2:8]2.Cl[C:24](OC1C=CC=CC=1)=[O:25].N1C=CC=CC=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>O1CCOCC1.C(Cl)(Cl)Cl>[N:39]1([C:24]([O:1][CH2:2][C:3]2[CH:4]=[C:5]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6](=[O:16])[N:7]3[C:12]=2[C:11]2[S:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8]3)=[O:25])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8083MorpholineHCID 15891Phenyl chloroformateHCID 14666699HCID 14666699, compound

Product 1

HCID 14666700HCID 14666700, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 0.59 g of 4,5-dihydro-10-(hydroxymethyl)-8-phenyl-7H-thieno[2,3-a]quinolizine-7-one in 15 ml of dioxane was treated with 0.38 ml of phenyl chloroformate and 0.27 ml of pyridine and stirred at room temperature for 2.5 hours. Then, 3 ml of morpholine were added and the mixture was stirred further until the reaction was completed. The mixture was diluted with chloroform, washed with 1N hydrochloric acid, 10 percent potassium bicarbonate solution and saturated sodium chloride solution, dried over magnesium sulfate and concentrated. By crystallization from ethanol, there was obtained pure (4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizin-10-yl)methyl 4-morpholine carboxylate of m.p. 163°-164°.

Workup

  1. stirringthe mixture was stirred further until the reaction
  2. washwashed with 1N hydrochloric acid, 10 percent potassium bicarbonate solution and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customBy crystallization from ethanol

Sources & evidence

ORD record
ord-3b3d557a660b466cb833a71340bc6c91
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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