1-Benzyl-4-piperidylamine → N-(1-Benzyl-4-piperidyl)-alpha-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetamide

HRID 1198907Notes

Reaction equation

HRID 1198907 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=O.[NH2:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:26][CH2:25]1>>[CH2:30]([N:27]1[CH2:28][CH2:29][CH:24]([NH:23][C:6](=[O:8])[CH2:5][O:4][C:3]2[CH:11]=[CH:12][C:13]([C:15]3[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=3)=[CH:14][C:2]=2[Cl:1])[CH2:25][CH2:26]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 4158521-Benzyl-4-piperidylamineHCID 14370696Ethyl alpha-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetate

Product 1

HCID 14370698N-(1-Benzyl-4-piperidyl)-alpha-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetamideYield 69.5%

Procedure

0.5 g (1.53 mmole) of ethyl α-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetate (prepared as described in Example 5) was mixed with 0.58 g (3.06 mmole) of 4-amino-1-benzylpiperidine, and the mixture was stirred at 120°-130° C. for 2.5 hours. The mixture was then cooled, after which it was subjected to column chromatography through silica gel and eluted with methylene chloride containing 2% v/v ethanol to give 0.5 g of a pale yellow oil. Trituration of this oil with ethanol yielded crystals, which were then recrystallized from ethanol, to give 0.33 g of the title compound as pale yellow fine crystals melting at 190°-191° C.

Workup

  1. temperatureThe mixture was then cooled
  2. washeluted with methylene chloride containing 2% v/v ethanol

Sources & evidence

ORD record
ord-d38e61a6d03f41db8977130d2083a37b
Source dataset
uspto-grants-1990_02
Patent number
US04898862

Reaction notes

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