Benzoyl chloride → 1-Benzoyl-4-bromopiperidine

HRID 1953805Notes

Reaction equation

HRID 1953805 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[Br:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C>C1COCC1>[C:1]([N:15]1[CH2:16][CH2:17][CH:12]([Br:11])[CH2:13][CH2:14]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 27346764-Bromopiperidine Hydrobromide

Product 1

HCID 156154171-Benzoyl-4-bromopiperidineYield 102.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzoyl chloride (1.41 g) was added to a solution of 4-bromopiperidine hydrobromide (2.45 g) in THF (30 ml) at 0° C., followed by triethylamine (2.2 g, 2.2 eq). The solution was stirred at room temperature for 1 h, and evaporated and. The residue was dissolved in dichloromethane (100 ml), washed with water, 1M HCl and saturated sodium bicarbonate, dried and evaporated to give the title compound as colourless oil (2.76 g, 100%).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  3. washwashed with water, 1M HCl and saturated sodium bicarbonate
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-5a3be90131314de5928df8f2e7b55486
Source dataset
uspto-grants-2000_09
Patent number
US06118001

Reaction notes

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