N-bromobutanimide → 3-[1-(5-Bromo-2-thienyl)-3-(methoxymethoxy)cyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine

HRID 503015Notes

Reaction equation

HRID 503015 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:8][C:7]([C:14]2[N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:17]3=[N:16][N:15]=2)([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH2:6]1.[Br:25]N1C(=O)CCC1=O>C(O)(=O)C.C(Cl)(Cl)Cl>[Br:25][C:11]1[S:10][C:9]([C:7]2([C:14]3[N:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:17]4=[N:16][N:15]=3)[CH2:8][CH:5]([O:4][CH2:3][O:2][CH3:1])[CH2:6]2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 684676073-[3-(Methoxymethoxy)-1-(2-thienyl)cyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine

Product 1

HCID 684698453-[1-(5-Bromo-2-thienyl)-3-(methoxymethoxy)cyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocineYield 93.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

3-[3-(Methoxymethoxy)-1-(2-thienyl)cyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (343 mg) was dissolved in acetic acid (3 ml) and then N-bromosuccinimide (193 mg) was added, followed by stirring at room temperature for 7 hours under light-shielding. The reaction solution was diluted with chloroform (40 ml) and then washed with water (10 ml), a 1M aqueous sodium hydroxide solution (10 ml), and brine (10 ml). The organic layer was dried and then concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (methanol:chloroform=2:98) to obtain 392 mg of 3-[1-(5-bromo-2-thienyl)-3-(methoxymethoxy)cyclobutyl]-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (reddish purple syrup).

Workup

  1. washwashed with water (10 ml)
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (methanol:chloroform=2:98)

Sources & evidence

ORD record
ord-2c3bb5b491fb46b9b61f6b9a583e1150
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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