Ammonium Chloride → HCID 20244223, compound

HRID 1632586Notes

Reaction equation

HRID 1632586 reaction equation
C[O:2][C:3]1C=C(CNCCCNCCCCNCCCNCC2C=CC(O)=C(OC)C=2)C=[CH:5][C:4]=1O.C(CC[CH:39]1N2[C:45]3[C:50]([CH2:51][CH2:52][CH:43]2[CH2:42][CH2:41][CH2:40]1)=[C:49]([OH:53])[CH:48]=[C:47]([O:54][CH:55]([CH2:57][CH2:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[CH3:56])[CH:46]=3)=O.[CH2:66]([Mg]I)[CH3:67].[Cl-].[NH4+:71]>C(OCC)C>[OH:53][C:49]1[CH:48]=[C:47]([O:54][CH:55]([CH2:57][CH2:58][CH2:59][C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH3:56])[CH:46]=[C:45]2[C:50]=1[CH:51]([CH2:5][CH2:4][CH:3]([OH:2])[CH2:66][CH3:67])[CH2:52][CH:43]1[CH2:42][CH2:41][CH2:40][CH2:39][N:71]12

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 131713909HCID 131713909, compoundHCID 178461634HCID 178461634, compound

Product 1

HCID 20244223HCID 20244223, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 598 mg. (1.42 mmole) dl-6-(2-formylethyl)-7-hydroxy-9-(5-phenyl-2-pentyloxy)-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline in 10 ml. ethyl ether is cooled in ice for 15 minutes. From a syringe, 1.58 ml. of 2.9M ethyl magnesium iodide is added slowly with stirring. The reaction mixture was allowed to warm to room temperature and stirred for three hours. Ammonium chloride crystals (ca. 100 mg.) was added to consume the unreacted Grignard reagent and the mixture stirred for 20 minutes. Ethyl acetate, 75 ml., and water, 50 ml., were added, the mixture stirred for a few minutes, and the layers separated. The aqueous layer was extracted with 50 ml. of ethyl acetate and the combined organic layers washed with 50 ml. each of water, brine and water again. The organic layer was dried over anhydrous magnesium sulfate and solvent evaporated in vacuo to obtain the crude product which is purified, if desired, by chromatography.

Workup

  1. stirringstirred for three hours
  2. customto consume the unreacted Grignard reagent
  3. stirringthe mixture stirred for 20 minutes
  4. addition, were added
  5. stirringthe mixture stirred for a few minutes
  6. customthe layers separated
  7. extractionThe aqueous layer was extracted with 50 ml
  8. washof ethyl acetate and the combined organic layers washed with 50 ml
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate and solvent
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-ed19382b6a5441adb46faa4bf602970f
Source dataset
uspto-grants-1984_10
Patent number
US04476131

Reaction notes

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