Benzyl Bromide → HCID 12354099, compound

HRID 1658511Notes

Reaction equation

HRID 1658511 reaction equation
[OH:1][C:2]1[C:7]2=[N:8][C:9]3[CH2:15][CH2:14][CH2:13][C:10]=3[C:11](=[O:12])[N:6]2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Na].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.[Cu]>[C:20]1([CH2:19][O:1][C:2]2[C:7]3=[N:8][C:9]4[CH2:15][CH2:14][CH2:13][C:10]=4[C:11](=[O:12])[N:6]3[CH:5]=[CH:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5360545SodiumHCID 12354095HCID 12354095, compound

Product 1

HCID 12354099HCID 12354099, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6.1 g. of 2,3-dihydro-5-hydroxycyclopenta[d]pyrido[1,2-a]pyrimidin-10(1H)-one in 100 ml of N,N-dimethylformamide is added, portionwise, a total of 1.6 g of a 50% dispersion of sodium hydride in mineral oil. A yellow precipitate of the sodium salt separates. The mixture is allowed to stir for 0.5 hour at room temperature, and then 6.2 g. of benzyl bromide dissolved in 25 ml of N,N-dimethylformamide is added, dropwise, followed by 100 mg. of copper bronze powder. The mixture is stirred and heated to 100°-110° and kept at that temperature for 2 hours. The hot solution is filtered, concentrated in vacuo, and the solid residue recrystallized from cyclohexane to give 7.2 g. of product, m.p. 150°-152°.

Workup

  1. additionis added
  2. stirringThe mixture is stirred
  3. temperatureheated to 100°-110°
  4. waitkept at that temperature for 2 hours
  5. filtrationThe hot solution is filtered
  6. concentrationconcentrated in vacuo
  7. customthe solid residue recrystallized from cyclohexane
  8. customto give 7.2 g

Sources & evidence

ORD record
ord-1728dd7f4fdd4829b924ed95071b3c4e
Source dataset
uspto-grants-1976_06
Patent number
US03965100

Reaction notes

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