Acetic Anhydride → HCID 20244221, compound

HRID 1632582Notes

Reaction equation

HRID 1632582 reaction equation
COC1C=C(CNCCCNCCCCNCCCNCC2C=CC(O)=C(OC)C=2)C=CC=1O.OCC[CH:38]1[N:43]2[C:44]3[C:49]([CH2:50][CH2:51][CH:42]2[CH2:41][CH2:40][CH2:39]1)=[C:48]([OH:52])[CH:47]=[C:46]([O:53][CH:54]([CH2:56][CH2:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[CH3:55])[CH:45]=3.C(N(CC)CC)C.[C:72]([O:75][C:76](=[O:78])[CH3:77])(=O)[CH3:73]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:76]([O:75][C:72]1[CH:47]=[C:46]([O:53][CH:54]([CH2:56][CH2:57][CH2:58][C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)[CH3:55])[CH:45]=[C:44]2[C:73]=1[CH:50]([CH2:49][CH2:48][OH:52])[CH2:51][CH:42]1[CH2:41][CH2:40][CH2:39][CH2:38][N:43]12)(=[O:78])[CH3:77]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 131713904HCID 131713904, compound

Product 1

HCID 20244221HCID 20244221, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.09 g. (0.01 mole) dl-6-(2-hydroxyethyl)-7-hydroxy-9-(5-phenyl-2-pentyloxy)-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline in 60 ml. methylene chloride containing 1.01 g. (0.01 mole) triethylamine is cooled to 0° C. while stirring in a nitrogen atmosphere. To this is added a solution of 1.22 g. (0.01 mole) 4-dimethylaminopyridine in 5 ml. of methylene chloride followed by 1.02 g. (0.01 mole) acetic anhydride. After stirring at 0°-5° C. for one hour, the mixture is allowed to warm to room temperature, extracted with methylene chloride and the extracts washed with sodium bicarbonate. After drying over anhydrous magnesium sulfate and evaporation of solvent, the desired product is obtained. It can be purified by column chromatography on silica gel if desired.

Workup

  1. additionTo this is added a solution of 1.22 g
  2. stirringAfter stirring at 0°-5° C. for one hour
  3. extractionextracted with methylene chloride
  4. washthe extracts washed with sodium bicarbonate
  5. dry with materialAfter drying over anhydrous magnesium sulfate and evaporation of solvent

Sources & evidence

ORD record
ord-94899f1b6b8a43358c3388170af4e250
Source dataset
uspto-grants-1984_10
Patent number
US04476131

Reaction notes

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