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Allyl bromide → HCID 23300004, compound

HRID 1952754
Notes
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Reaction equation

HRID 1952754 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2([CH3:28])[C:20](=[O:21])[NH:19][C:18]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[N:17]2)[CH2:11][CH2:10]1.[CH2:29](Br)[CH:30]=[CH2:31].[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>O1CCCC1>[CH2:31]([N:19]1[C:20](=[O:21])[C:16]([CH2:15][N:12]2[CH2:13][CH2:14][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:10][CH2:11]2)([CH3:28])[N:17]=[C:18]1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH:30]=[CH2:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 23300006HCID 23300006, compound

Product 1

HCID 23300004HCID 23300004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]-4-methyl-2-(3-pyridyl)-2-imidazolin-5-one (3.7 g; prepared in a similar manner to that described in Example 36), allyl bromide (1.05 ml), finely-powdered potassium hydroxide (0.79 g), 18-Crown-6 (0.26 g) and tetrahydrofuran (50 ml) was stirred at ambient temperature under nitrogen for 120 hours, then poured onto ice-water (30 ml). The product was extracted into ethyl acetate, the extracts were dried (MgSO4), and the solvent was removed in vacuo. The residue was purified by flash chromatography over silica using a 9:1 mixture of ethyl acetate and ethanol as eluant. Appropriate fractions were combined, and the solvents removed in vacuo to leave 1-allyl-4-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]-4-methyl-2-(3-pyridyl)-2-imidazolin-5-one as an off-white solid (0.25 g), m.p. 66-69° C.

Workup

  1. customprepared in a similar manner to that
  2. additionpoured onto ice-water (30 ml)
  3. extractionThe product was extracted into ethyl acetate
  4. dry with materialthe extracts were dried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by flash chromatography over silica using
  7. additiona 9:1 mixture of ethyl acetate and ethanol as eluant
  8. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-c43a877ab27c4bcab88778da9c1b5f9f
Source dataset
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06114334

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes