Hydrochloric Acid → HCID 53328147, compound

HRID 1190886Notes

Reaction equation

HRID 1190886 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[NH2:5].Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1.Cl>C(#N)C>[Cl:32][C:28]1[CH:27]=[C:26]2[C:31]([C:22]([NH:5][C:4]3[CH:6]=[C:7]([CH2:15][N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)[C:8]([N:9]4[CH2:10][CH2:11][O:12][CH2:13][CH2:14]4)=[C:2]([CH3:1])[CH:3]=3)=[CH:23][CH:24]=[N:25]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68664,7-DichloroquinolineHCID 53328723HCID 53328723, compound

Product 1

HCID 53328147HCID 53328147, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Methyl-4-(morpholin-4-yl)-5-(pyrrolidin-1-ylmethyl)aniline (46 mg, 0.17 mmol) and 4,7-dichloroquinoline (40 mg, 0.20 mmol) were refluxed overnight in 5 mL of acetonitrile with 0.51 mL of HCl 1M. The reaction mixture was then evaporated and purified by flash chromatography (DCM/MeOH/NH4OH//95/5/0 to 90/10/1) to yield expected compound as a white solid (53 mg, 71% yield); m/z (ESI) 437.3 [M+H]+;

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by flash chromatography (DCM/MeOH/NH4OH//95/5/0 to 90/10/1)

Sources & evidence

ORD record
ord-4c1c503ecabc4cb888c077b46c960b71
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

Loading…