Acetyl chloride → HCID 18967525, compound

HRID 235119Notes

Reaction equation

HRID 235119 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27].CO.C(OCC)(=O)C>C(#N)C>[C:26]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21584119Ethylacetate methanolHCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 18967525HCID 18967525, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.238 g, 0.986 mmol) and triethylamine (0.144 mL, 1.08 mmol) in acetonitrile (12 mL) was chilled to 0° C. and acetyl chloride (0.077 mL, 1.08 mmol) was added all at once. The mixture was heated to reflux for 7 hours and cooled to room temperature. (TLC with 40% methanol/ethyl acetate indicated that the reaction was complete.) The solvent was removed at reduced pressure and the residue was taken up in methylene chloride. The organic solution was extracted with saturated sodium bicarbonate and brine, then it was dried over calcium sulfate and concentrated to a light tan solid (0.115 g). Trituration with hexane gave 0.09 g (33%) of the title product as a tan solid: mp 173°-177° C. A sample recrystallized from ethyl acetate was submitted for analysis: mp 177°-180° C. HRMS m/e calculated for C17H29N3O: 283.1682. Observed m/e: 283.1678.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 7 hours
  3. custom) The solvent was removed at reduced pressure
  4. extractionThe organic solution was extracted with saturated sodium bicarbonate and brine
  5. dry with materialit was dried over calcium sulfate
  6. concentrationconcentrated to a light tan solid (0.115 g)

Sources & evidence

ORD record
ord-974311f305f142b2bc4260a0fbf20216
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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