Acetyl chloride → Acetamide, N-(4-((1-methyl-4-phenyl-4-piperidinyl)oxy)phenyl)-

HRID 1156035

Reaction equation

HRID 1156035 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:25]=[CH:24][C:9]([O:10][C:11]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:8][CH:7]=1.C(N(CC)CC)C>C1C=CC=CC=1>[NH:5]([C:6]1[CH:25]=[CH:24][C:9]([O:10][C:11]2([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]2)=[CH:8][CH:7]=1)[C:1]([CH3:2])=[O:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 3060392Piperidine, 4-(p-aminophenoxy)-1-methyl-4-phenyl-

Product 1

HCID 3060397Acetamide, N-(4-((1-methyl-4-phenyl-4-piperidinyl)oxy)phenyl)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 0.85 g of acetyl chloride in 5 ml of benzene is added dropwise to a solution of 2.8 g of 4-(4-aminophenoxy)-1-methyl-4-phenylpiperidine and 1.1 g of triethylamine in 10 ml of benzene. After stirring the mixture at room temperature for 6 hours, it is concentrated; the resulting residue is taken up with 30 ml each of water and diethyl ether; the obtained mixture is shaken thoroughly, and the organic phase is separated off, dried over sodium sulfate and concentrated. 2.8 g of the title compound remain as a viscous yellow oil which crystallizes (m.p. 143° to 144° C.) from diethylether after standing for several days.

Workup

  1. concentrationit is concentrated
  2. stirringthe obtained mixture is shaken thoroughly
  3. customthe organic phase is separated off
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customcrystallizes (m.p. 143° to 144° C.) from diethylether
  7. waitafter standing for several days

Sources & evidence

ORD record
ord-870e1b1a003c4c58bf0b300d6fd1bbc5
Source dataset
uspto-grants-1982_06
Patent number
US04333942

Linked notes

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