Iodine → 1-Methyl-3-(3,4-dichlorophenacyl)piperidine

HRID 1657830Notes

Reaction equation

HRID 1657830 reaction equation
[Mg].[CH3:2][N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9]Cl)[CH2:4]1.II.FC1C=CC(C#N)=CC=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[Cl:31])[C:26]#N.[Cl-].[NH4+].[OH2:34]>>[CH3:2][N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][C:26]([C:25]2[CH:28]=[CH:29][C:30]([Cl:31])=[C:23]([Cl:22])[CH:24]=2)=[O:34])[CH2:4]1

Participants

8

Reactant 7

HCID 807IodineHCID 962WaterHCID 145174-FluorobenzonitrileHCID 25517Ammonium Chloride2×HCID 810513,4-DichlorobenzonitrileHCID 1036743-(Chloromethyl)-1-methylpiperidineHCID 5462224Magnesium

Product 1

HCID 215303621-Methyl-3-(3,4-dichlorophenacyl)piperidine

Procedure

The procedure of Example 3 was repeated, except that the Grignard reagent was prepared from 2.0 g of magnesium turnings and 10.3 g of 1-methyl-3-chloromethylpiperidine and the use of iodine was omitted, the 4-fluorobenzonitrile was replaced with 13.3 g of 3,4-dichlorobenzonitrile, the ammonium chloride solution was replaced with 100 ml of water containing 8 of ammonium chloride, the work-up procedure generally followed that described in Example 2, and the maleate salt procedure was not employed. The crude product, 16.2 g, was recrystallized first from acetone and then from hexane to give 7.4 g of 1-methyl-3-(3,4-dichlorophenacyl)piperidine, mp 69°-71°. The following elemental analysis was obtained:

Workup

  1. customThe crude product, 16.2 g, was recrystallized first from acetone

Sources & evidence

ORD record
ord-a08127c5a4b646e8b30f348a16481527
Source dataset
uspto-grants-1976_06
Patent number
US03962257

Reaction notes

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