Benzyl Bromide → 2-(Piperidin-4-yl)-1,3-benzoxazole

HRID 1704627Notes

Reaction equation

HRID 1704627 reaction equation
C(Br)C1C=CC=CC=1.[N:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][CH:10]=1>C(#N)C>[NH:9]1[CH2:10][CH2:11][CH:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 16804Benzoxazole, 2-(4-pyridyl)-

Product 1

HCID 7704612-(Piperidin-4-yl)-1,3-benzoxazoleYield 69.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 1.71 g of benzyl bromide in 10 ml of acetonitrile is added to a solution of 1.96 g of 2-(4-pyridinyl)benzoxazole in 25 ml of hot acetonitrile. After 10 minutes the product begins to crystallize out of solution. The mixture is heated on the steam bath for 2 hours and then diluted with ether and filtered. The crude solid is dissolved in 50 ml of 1:1 methanol-water and treated portionwise with 2 g of sodium borohydride. The mixture is diluted with water and 2.4 g of the solid product is collected. The 2.4 g of solid is dissolved in 150 ml of ethanol, 2 g of 5% paladium on carbon is added, and the mixture is placed on the Parr hydrogenator under 50 psi hydrogen. The mixture is filtered, and the filtrate evaporated in vacuo to give 1.4 g of the title compound.

Workup

  1. customto crystallize out of solution
  2. temperatureThe mixture is heated on the steam bath for 2 hours
  3. additiondiluted with ether
  4. filtrationfiltered
  5. dissolutionThe crude solid is dissolved in 50 ml of 1:1 methanol-water
  6. additiontreated portionwise with 2 g of sodium borohydride
  7. additionThe mixture is diluted with water and 2.4 g of the solid product
  8. customis collected
  9. dissolutionThe 2.4 g of solid is dissolved in 150 ml of ethanol
  10. addition2 g of 5% paladium on carbon is added
  11. filtrationThe mixture is filtered
  12. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-e2321cc1ba034c22adeef7b653e39767
Source dataset
uspto-grants-1978_11
Patent number
US04127579

Reaction notes

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