Acetyl chloride → HCID 19833121, compound

HRID 1639390Notes

Reaction equation

HRID 1639390 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+].Cl.Cl[CH2:23][CH2:24][CH2:25][NH2:26].C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35]>C1(C)C=CC=CC=1.O>[C:34]([N:26]1[C:7]2[CH2:6][CH:5]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]3[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:9]=3[C:8]=2[CH2:23][CH2:24][CH2:25]1)(=[O:36])[CH3:35]

Participants

8

Reactant 5

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 114690951-Propanamine, 3-chloro-, hydrochlorideHCID 19833160HCID 19833160, compound

Product 1

HCID 19833121HCID 19833121, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 73.3 g (0.23 mol) of 6-chloro-3,4-dihydro-4-phenyl-2(1H)-naphthalenone in 1.5 l of toluene is treated with 32.4 g (0.58 mol) of potassium hydroxide and 83.7 g (0.64 mol) of 3-chloropropylamine hydrochloride and boiled on a water separator for 42 hours. After cooling to room temperature, there are added thereto 79 ml (0.56 mol) of triethylamine and dropwise 29.7 ml (0.42 mol) of acetyl chloride in 250 ml of toluene. The mixture is stirred for 1 hour, extracted with ethyl acetate/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography over silica gel with hexane-ethyl acetate (4:1) and then with hexane-ethyl acetate (1:1) and recrystallization from ethyl acetate gives 4-acetyl-8-chloro-1,2,3,4,5,6-hexahydro-6-phenylbenzo[f]quinoline as beige crystals with melting point 167°-168°.

Workup

  1. additionthere are added
  2. extractionextracted with ethyl acetate/water
  3. dry with materialdried with magnesium sulfate
  4. distillationthe solvent is distilled in a vacuum
  5. customChromatography over silica gel with hexane-ethyl acetate (4:1) and then with hexane-ethyl acetate (1:1) and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-01c9dc454c874b5aa6dfdb7ce2c40932
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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