8-Methoxy-2,3,4,5,6,7-hexahydroazocine → 3-[3-(Methoxymethoxy)-1-(2-thienyl)cyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine

HRID 503010Notes

Reaction equation

HRID 503010 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:8][C:7]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)([C:9]([NH:11][NH2:12])=O)[CH2:6]1.CO[C:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:8][C:7]([C:9]2[N:27]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]3=[N:12][N:11]=2)([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 122610598-Methoxy-2,3,4,5,6,7-hexahydroazocineHCID 684700873-(Methoxymethoxy)-1-(2-thienyl)cyclobutanecarbohydrazide

Product 1

HCID 684676073-[3-(Methoxymethoxy)-1-(2-thienyl)cyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocineYield 83.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(Methoxymethoxy)-1-(2-thienyl)cyclobutanecarbohydrazide (5.45 g) and 8-methoxy-2,3,4,5,6,7-hexahydroazocine (4.51 g) were heated in toluene (60 ml) at 110° C. for 19 hours. After concentration, the concentrate was purified by silica gel column chromatography (methanol:chloroform=2:98) to obtain 3-[3-(methoxymethoxy)-1-(2-thienyl)cyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (6.14 g).

Workup

  1. concentrationAfter concentration
  2. customthe concentrate was purified by silica gel column chromatography (methanol:chloroform=2:98)

Sources & evidence

ORD record
ord-a880ab33f4734544a0475a7d329ef91c
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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