Hydrochloric Acid → Hydrochloric Acid

HRID 1087533Notes

Reaction equation

HRID 1087533 reaction equation
[O:1]=[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([C:18]#[N:19])=[C:8]2[N:3]1[CH2:4][CH2:5][C:6]1[CH:22]=[CH:21][S:20][C:7]=12.[ClH:23].[OH-].[Na+]>O1CCCC1>[ClH:23].[ClH:23].[NH2:19][CH2:18][C:9]1[CH:10]=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2](=[O:1])[N:3]2[C:8]=1[C:7]1[S:20][CH:21]=[CH:22][C:6]=1[CH2:5][CH2:4]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14770040HCID 14770040, compound

Product 2

HCID 313Hydrochloric AcidHCID 19020418HCID 19020418, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.5 g of 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carbonitrile in 15 ml of tetrahydrofuran was treated with 20 ml of a 1M BH3 /tetrahydrofuran solution and stirred at room temperature until the reaction was finished. The mixture was then acidified cautiously with 2N hydrochloric acid while cooling with ice, heated to boiling for a short time and made alkaline with 2N sodium hydroxide solution. The tetrahydrofuran was removed, in vacuo and the aqueous residue was extracted with chloroform. The organic phase was washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel with chloroform/methanol (19:1). After treatment with methanolic hydrochloric acid, there was obtained pure 10-(aminomethyl)-4,5-dihydro-8-phenyl-7H-thieno[2,3-a]quinolizin-7-one hydrochloride of m.p. 254°-255°.

Workup

  1. temperaturewhile cooling with ice
  2. temperatureheated
  3. customThe tetrahydrofuran was removed, in vacuo
  4. extractionthe aqueous residue was extracted with chloroform
  5. washThe organic phase was washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel with chloroform/methanol (19:1)

Sources & evidence

ORD record
ord-1ec1420204e343e98d8579861d1460e8
Source dataset
uspto-grants-1991_07
Patent number
US05036066

Reaction notes

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