2-Bromobenzyl bromide → HCID 19107064, compound

HRID 1460599Notes

Reaction equation

HRID 1460599 reaction equation
CC(C)([O-])C.[K+].[CH3:7][CH:8]1[CH:13]([C:14]([OH:16])=[O:15])[C:12](=[O:17])[CH2:11][CH2:10][N:9]1[C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Br:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29]Br>C(O)(C)(C)C>[CH3:7][CH:8]1[C:13]([CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[Br:26])([C:14]([OH:16])=[O:15])[C:12](=[O:17])[CH2:11][CH2:10][N:9]1[C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 769652-Bromobenzyl bromideHCID 19107122HCID 19107122, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19107064HCID 19107064, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a solution of potassium t-butoxide (16.8 g, 0.15 mol) in t-butanol (300 ml) was added methyl 1-benzoyl-4-oxo-3-piperidinecarboxylic acid (36.1 g, 0.146 mol) according to the method of G. Stork, J. Am. Chem. Soc. 68, 1053 (1946). The mixture was stirred 1 hour and 2-bromobenzyl bromide was added dropwise in a solution of t-butanol. The reaction was heated to reflux for 2 days, cooled and filtered. The salts were washed with ether and the organic filtrate was washed with 5% hydrochloric acid (100 ml), saturated sodium bicarbonate (100 ml), water (100 ml) and saturated sodium chloride (100 ml). The organic layer was dried (MgSO4), filtered, and concentrated to yield a crude oil. The material was recrystallized from isopropyl ether to yield a pale yellow solid (23.4 g, 37%) An additional recrystallization produced the title compound a white solid, mp 105°-107° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 days
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe salts were washed with ether
  6. washthe organic filtrate was washed with 5% hydrochloric acid (100 ml), saturated sodium bicarbonate (100 ml), water (100 ml) and saturated sodium chloride (100 ml)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield a crude oil
  11. customThe material was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-5450b99ad46d45c896be5e8a715ffb31
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

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