HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → 6,8-Dichloro-2-[[4-(4-fluorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridine

HRID 1416260
Notes
Print preview

Reaction equation

HRID 1416260 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Cl:13])[C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C(N(CC)CC)C>C(O)CO>[Cl:1][C:2]1[CH:3]=[C:4]([Cl:13])[C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:24]3[CH2:23][CH2:22][N:21]([C:18]4[CH:17]=[CH:16][C:15]([F:14])=[CH:20][CH:19]=4)[CH2:26][CH2:25]3)[N:10]=2)[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 47730446,8-Dichloro-2-(chloromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 193671126,8-Dichloro-2-[[4-(4-fluorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridineYield 62.8%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
82.5 °C

Procedure

A mixture of 6,8-dichloro-2-(chloromethyl)imidazo[1,2-α]pyridine (0.3064 g), 1-(4-fluorophenyl)piperazine (Aldrich; 0.266 g), triethylamine (Aldrich; 0.21 mL), and ethylene glycol (2 mL) is stirred for 1 h at 80-85° C. After cooling, the mixture is partitioned between water and dichloromethane and the organic layers are washed with brine and dried over MgSO4. After concentration under reduced pressure, the residue is chromatographed on silica gel using methanol/dichloromethane (4/96) and the appropriate fractions are combined and concentrated and the residue is crystallized from ethyl acetate/hexane to give 0.3098 g of the title compound; mp 126.5-127.5° C.; MS m/z 378, 380; IR (mineral oil) 1510, 1215, 1335, 826, 1224 cm-1 ; 1H NMR (CDCl3) δ2.75, 3.15, 3.83, 6.87, 6.96, 7.26, 7.62, 8.09.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between water and dichloromethane
  3. washthe organic layers are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue is chromatographed on silica gel
  7. concentrationconcentrated
  8. customthe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1c543c94d1de4a9c8bfd999e7477df7e
Source dataset
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05912246

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes