5-(3-Pyridinyl)pentanoic acid → 4-(2,2-Diphenylethenyl)-1-[1-oxo-5-(3-pyridinyl)pentyl]piperidine

HRID 1249570Notes

Reaction equation

HRID 1249570 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH2:28][CH2:29][CH2:30][C:31](O)=[O:32])[CH:22]=1>>[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]2[CH2:10][CH2:11][N:12]([C:31](=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)[CH2:13][CH2:14]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 114807975-(3-Pyridinyl)pentanoic acidHCID 13754500HCID 13754500, compound

Product 1

HCID 137545234-(2,2-Diphenylethenyl)-1-[1-oxo-5-(3-pyridinyl)pentyl]piperidineYield 94.2%

Procedure

The title compound was prepared in a manner similar to that employed for the compound of example 10 starting with 5.27 g of 4-(2,2-diphenylethenyl)piperidine and the acid chloride prepared from 6.5 g of 3-pyridine pentanoic acid. The toluene extracts were evaporated and chromatographed on a Waters Prep 500 using silica gel columns and eluting with 98:2 ethyl acetate-triethylamine. Evaporation of the combined product fractions gave 8.0 g (94%) of crude 4-(2,2-diphenylethenyl)-1-[1-oxo-5-(3-pyridinyl)pentyl]piperidine. Crystallization of a small portion from ether gave analytically pure 4-(2,2-diphenylethenyl)-1-[1-oxo-5-(3-pyridinyl)pentyl]piperidine, mp 82°-84° C. Analysis Calculated for C29H32N2O: C, 82.04; H, 7.60; N, 6.60. Found: C, 81.88; H, 7.63; N, 6.67.

Workup

  1. customThe title compound was prepared in a manner similar to
  2. customThe toluene extracts were evaporated
  3. customchromatographed on a Waters Prep 500 using silica gel columns
  4. washeluting with 98:2 ethyl acetate-triethylamine
  5. customEvaporation of the combined product fractions

Sources & evidence

ORD record
ord-ee5f3ad67533447cbffc179a26f52ceb
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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