Benzyl Bromide → HCID 12354099, compound

HRID 1658500Notes

Reaction equation

HRID 1658500 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.C(=O)(O)[O-].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(CC)=O>[C:22]1([CH2:21][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:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516893Potassium BicarbonateHCID 12354095HCID 12354095, compound

Product 1

HCID 12354099HCID 12354099, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 2,3-dihydro-5-hydroxycyclopenta[d]pyrido[1,2-a]pyrimidin-10(1H)-one prepared as described in Example 1, (6.1 g), 9.9 g of anhydrous potassium bicarbonate, 6.2 g of benzyl bromide, and 300 ml of ethyl methyl ketone is stirred and slowly heated to reflux. Stirring and heating under reflux is continued for 18 hours. The hot solution is filtered to remove inorganic salts and the ethyl methyl ketone filtrate is concentrated in vacuo to give 10.0 g of crude product; this, when recrystallized from 1000 ml of cyclohexane, and the crystalline solid dried at 78° for 2 hours, gives 6.0 g of product, mp 150°-152°.

Workup

  1. customprepared
  2. temperatureslowly heated to reflux
  3. stirringStirring
  4. temperatureheating
  5. temperatureunder reflux
  6. filtrationThe hot solution is filtered
  7. customto remove inorganic salts
  8. concentrationthe ethyl methyl ketone filtrate is concentrated in vacuo
  9. customto give 10.0 g of crude product
  10. customthis, when recrystallized from 1000 ml of cyclohexane
  11. customthe crystalline solid dried at 78° for 2 hours

Sources & evidence

ORD record
ord-77c23c98dbfe4e49a054311ad39f9b1c
Source dataset
uspto-grants-1976_06
Patent number
US03965100

Reaction notes

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