Allyl bromide → HCID 23300027, compound

HRID 1952755Notes

Reaction equation

HRID 1952755 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[O:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4([CH3:34])[C:26](=[O:27])[NH:25][C:24]([C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)=[N:23]4)[CH2:17][CH2:16]3)[C:9]=2[O:8][CH2:7][CH2:6]1.[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>O1CCCC1>[CH2:1]([N:25]1[C:26](=[O:27])[C:22]([CH2:21][N:18]2[CH2:17][CH2:16][N:15]([C:14]3[C:9]4[O:8][CH2:7][CH2:6][O:5][C:10]=4[CH:11]=[CH:12][CH:13]=3)[CH2:20][CH2:19]2)([CH3:34])[N:23]=[C:24]1[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 23299975HCID 23299975, compound

Product 1

HCID 23300027HCID 23300027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of allyl bromide (0.7 ml) in dry tetrahydrofuran (5 ml) was added dropwise at 0° C. under nitrogen to a stirred mixture of 4-[4-(1,4-benzodioxan-5-yl)piperazin-1-ylmethyl]-4-methyl-2-(3-pyridyl)-2-imidazolin-5-one (2.86 g; prepared in a similar manner to that described in Example 40), powdered potassium hydroxide (0.57 g) and 18-Crown-6 (0.18 g) in dry tetrahydrofuran (60 ml). The mixture was stirred at ambient temperature for 17 hours then poured onto ice-water (30 ml) and the product extracted into ether. The extracts were dried (MgSO4) and the solvents removed in vacuo to yield a foam which was triturated with ether. The precipitate was collected by filtration to yield 1-allyl-4-[4-(1,4-benzodioxan-5-yl)piperazin-1-ylmethyl]-4-methyl-2-(3-pyridyl)-2-imidazolin-5-one as a solid (0.53 g), m.p. 102-105° C.

Workup

  1. customprepared in a similar manner to that
  2. additionthen poured onto ice-water (30 ml)
  3. extractionthe product extracted into ether
  4. dry with materialThe extracts were dried (MgSO4)
  5. customthe solvents removed in vacuo
  6. customto yield a foam which
  7. customwas triturated with ether
  8. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-be42e387ce5a4ee382e00efdfce87760
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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