Piperidine → HCID 59292452, compound

HRID 1685110Notes

Reaction equation

HRID 1685110 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Br)=[O:7].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C1C=CC=CC=1>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([C:6]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:7])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 3847029HCID 3847029, compound

Product 1

HCID 59292452HCID 59292452, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 25 mL round bottom flask was added 3-bromomethyl-benzoyl bromide (1.39 g, 5 mmol) and benzene (5 mL). The flask was cooled to 0° C. with an ice bath and piperidine (852 mg, 2 eq) in benzene (3.3 mL) was added slowly. The reaction was stirred at 0° C. for three hours. The precipitate was removed by filtration on a Buchner funnel. The filtrate was concentrated to an oil which was purified by column chromatography with 20% ethyl acetate in hexanes to give the titled compound as a clear oil (578 mg, 41% yield).

Workup

  1. customThe precipitate was removed by filtration on a Buchner funnel
  2. concentrationThe filtrate was concentrated to an oil which
  3. customwas purified by column chromatography with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-95f11bfd1fca42ef9a37c2c0c1607162
Source dataset
uspto-grants-2012_04
Patent number
US08148367B2

Reaction notes

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