Acetyl chloride → HCID 12788523, compound

HRID 2295444Notes

Reaction equation

HRID 2295444 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Cl.Cl.[NH2:7][C:8]1[CH:27]=[CH:26][C:11]([O:12][C@H:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C@H:14]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:1]([NH:7][C:8]1[CH:27]=[CH:26][C:11]([O:12][C@H:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C@H:14]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 12788411HCID 12788411, compound

Product 1

HCID 12788523HCID 12788523, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1.4 ml of acetyl chloride in 75 ml of chloroform is added dropwise under nitrogen over a 15-minute period to a solution of 5.05 g of the free base of cis-4-(4-aminophenoxy)-1-methyl-3-phenylpiperidine of Example 8 in 150 ml of dry chloroform containing 2.74 ml of triethylamine. The pot temperature reaches a maximum of 28° C. The reaction is complete in 30 minutes. The chloroform solution is washed with 10% aqueous NaOH solution, then with saturated aqueous NaCl solution, dried over anhydrous Na2SO4 and concentrated in vacuo to a foam which solidifies upon trituration with hexane. The hexane mixture is briefly heated to boiling, then cooled to room temperature and allowed to stand for 30 minutes before filtering. A crude solid results, mp s 172°, 173°-175° C. Recrystallization from toluene affords cis-4-(4-acetamidophenoxy)-1-methyl-3-phenylpiperidine, mp 174.5°-176.5° C.

Workup

  1. customa maximum of 28° C
  2. washThe chloroform solution is washed with 10% aqueous NaOH solution
  3. dry with materialwith saturated aqueous NaCl solution, dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo to a foam which
  5. temperatureThe hexane mixture is briefly heated
  6. waitto stand for 30 minutes
  7. filtrationbefore filtering
  8. customA crude solid results
  9. customs 172°, 173°-175° C
  10. customRecrystallization from toluene

Sources & evidence

ORD record
ord-a62f35c3026c40729a030ab6a22f31b9
Source dataset
uspto-grants-1984_01
Patent number
US04424357

Reaction notes

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