Acetyl chloride → HCID 19833123, compound

HRID 1639363Notes

Reaction equation

HRID 1639363 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([N:7]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:12]=3[C:11]=2[CH2:10][CH2:9][CH2:8]1)=[O:6].C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>C(Cl)Cl>[Cl:21][C:18]1[CH:19]=[CH:20][C:12]2[C:11]3[CH2:10][CH2:9][CH2:8][N:7]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][NH:1][C:29](=[O:31])[CH3:30])[C:16]=3[CH2:15][CH2:14][C:13]=2[CH:17]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19833126HCID 19833126, compound

Product 1

HCID 19833123HCID 19833123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 5.09 g (0.015 mol) of 4-(4-aminobutyryl)-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline in 50 ml of methylene chloride are added 5 ml (0.036 mol) of triethylamine and then at 0° 1.33 ml (0.019 mol) of acetyl chloride dissolved in 15 ml of methylene chloride, and the mixture is stirred at room temperature for 1 hour. Then, the mixture is extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Crystallization from methylene chloride/ether, chromatography on silica gel with ethyl acetate/methanol (9:1) and renewed crystallization from methylene chloride/ether gives N-[4-[8-chloro-2,3,5,6,-tetrahydrobenzo[f]quinolin-4(1H)-yl]-4-oxobutyl]acetamide as white crystals with melting point 142°-143°.

Workup

  1. extractionThen, the mixture is extracted with methylene chloride/water
  2. dry with materialdried with magnesium sulfate
  3. distillationthe solvent is distilled in a vacuum
  4. customCrystallization from methylene chloride/ether, chromatography on silica gel with ethyl acetate/methanol (9:1)
  5. customcrystallization from methylene chloride/ether

Sources & evidence

ORD record
ord-957e509777f0401b9a3113b8f1b2bccc
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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