Piperidine → 2-Bromo-1-(1-piperidinyl)-1-propanone

HRID 1462024Notes

Reaction equation

HRID 1462024 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:7][CH:8]([CH3:12])[C:9](Br)=[O:10]>C1(C)C=CC=CC=1>[Br:7][CH:8]([CH3:12])[C:9]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:10]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 130366062-Bromo-1-(1-piperidinyl)-1-propanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

Piperidine (73.3 grams; 0.91 moles) is dissolved in 400 cc of toluene and the solution is cooled to -10° C. There is added dropwise, (45.3 cc; 0.45 moles) of 2-bromopropionyl bromide while the temperature is not allowed to exceed -5° C. over a period of three hours. The mixture is stirred again for four hours, while the temperature is allowed to rise, then the mixture is filtered and the filtrate is evaporated under reduced pressure. The product boils at 102° C. (0.3 mm); IR (neat) νmax: 2940, 2860, 1650, 1450, 1380, 1260, 1140, 1020 cm-1. The product is a liquid very irritating to the skin and mucosae.

Workup

  1. additionThere is added dropwise
  2. filtrationthe mixture is filtered
  3. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-6704d96b2fd749b2984a06c0864a0773
Source dataset
uspto-grants-1984_07
Patent number
US04457931

Reaction notes

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