Pyridine → HCID 14666700, compound

HRID 1109593Notes

Reaction equation

HRID 1109593 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-5af07d5c168441f8b807881843993ea4
Source dataset
uspto-grants-1994_06
Patent number
US05321021

Reaction notes

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