1,4-Dibromobutane → HCID 53328350, compound

HRID 1190884Notes

Reaction equation

HRID 1190884 reaction equation
Cl.[CH3:2][C:3]1[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:5]([CH2:12][NH2:13])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([CH2:12][N:13]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:4]=1[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 53328347HCID 53328347, compound

Product 1

HCID 53328350HCID 53328350, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of [3-Methyl-2-(morpholin-4-yl)-5-nitrophenyl]methanamine hydrochloride (160 mg, 0.56 mmol), 1,4-dibromobutane (80 μL, 0.67 mmol) and K2CO3 (542 mg, 3.92 mmol) in 10 mL of acetonitrile was heated at 60° C. for 48 h. After filtration and evaporation of the filtrate, the residue was purified by flash chromatography (DCM/MeOH/NH4OH//9/1/0.1) to yield expected compound as a pale yellow oil (100 mg, 58% yield); m/z (ESI) 306.3 [M+H]+.

Workup

  1. filtrationAfter filtration and evaporation of the filtrate
  2. customthe residue was purified by flash chromatography (DCM/MeOH/NH4OH//9/1/0.1)

Sources & evidence

ORD record
ord-a94c0bf5349847f38fa1ebdc4888bbd6
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

Loading…