Benzyl Bromide → HCID 16459886, compound

HRID 1457610Notes

Reaction equation

HRID 1457610 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[CH2:16]([N:1]1[CH2:2][CH2:3][CH:4]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:6]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 16004294N-(Phenylmethyl)-4-piperidinemethanamine

Product 1

HCID 16459886HCID 16459886, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under ice-cooling, to 200 ml of a tetrahydrofuran (THF) solution containing 5.0 g of N-(4-piperidylmethyl)-N-benzylamine was added dropwise 50 ml of a THF solution containing 2.9 ml of benzyl bromide. After stirring the mixture at the same temperature for one hour, THF was removed from the reaction mixture under reduced pressure and a saturated sodium hydrogen carbonate aqueous solution was added to the residue. The mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. Precipitated crystals were recrystallized from an ethanol solution to give 3.6 g of N-(1-benzylpiperidin-4-ylmethyl)-N-benzylamine (yield: 50%, melting point: 240° C. or higher).

Workup

  1. customTHF was removed from the reaction mixture under reduced pressure
  2. additiona saturated sodium hydrogen carbonate aqueous solution was added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe extract was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customPrecipitated crystals
  8. customwere recrystallized from an ethanol solution

Sources & evidence

ORD record
ord-becb89b4c28341b3b0e97a7d16d6830a
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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