Piperidine → HCID 131710316, compound

HRID 1657829Notes

Reaction equation

HRID 1657829 reaction equation
ClC1C=CC(C#N)=CC=1.C(#N)C1C=CC(OC)=CC=1.[CH3:20][N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([CH2:27][C:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[O:29])[CH2:22]1.N1CCCCC1.[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48]>>[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48].[CH3:20][N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([CH2:27][C:28]([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)=[O:29])[CH2:22]1

Participants

6

Reactant 5

HCID 8082PiperidineHCID 121634-ChlorobenzonitrileHCID 701294-MethoxybenzonitrileHCID 444266Maleic AcidHCID 21530351HCID 21530351, compound

Product 1

HCID 131710316HCID 131710316, compound

Procedure

The procedure of Example 6 was repeated, using 82 ml of the same Grignard reagent solution, except that the 4-chlorobenzonitrile was replaced with 6.2 g of anisonitrile. The yield of crude 1-methyl-3-(4-methoxyphenacyl)piperidine was 7.3 g, bp 134°-138°/0.1 mm. Conversion of the piperidine compound to the maleate salt utilized 4.4 g of maleic acid with appropriate increases in solvent volumes. The crude salt thus obtained, 10.7 g, mp 91°-94°, was recrystallized to give 9.5 g of 1-methyl-3-(4-methoxyphenacyl)piperidine, maleate salt, mp 89°-92°. The following elemental analysis was obtained:

Workup

  1. temperaturewith appropriate increases in solvent volumes
  2. customThe crude salt thus obtained
  3. custom10.7 g, mp 91°-94°, was recrystallized

Sources & evidence

ORD record
ord-09087dc50199444095c2eca52395a0b2
Source dataset
uspto-grants-1976_06
Patent number
US03962257

Reaction notes

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