Diisopropylethylamine → HCID 57831211, compound

HRID 1642021Notes

Reaction equation

HRID 1642021 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][N:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1.Cl.O.[NH:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1.C(N(CC)C(C)C)(C)C>CS(C)=O>[CH3:14][N:12]1[N:11]=[N:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:17]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]3)=[CH:4][CH:5]=2)=[N:13]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5893295-(4-Bromomethylphenyl)-2-methyl-2H-tetrazoleHCID 2723901Piperonylamine

Product 1

HCID 57831211HCID 57831211, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 23 grams (0.091 mole) of 5-[4-(bromomethyl)phenyl]-2-methyl-1,2,3,4-tetrazole, 14 grams (0.091 mole) of 4-piperidone monohydrate hydrochloride, and 47 mL (3 equivalents) of N,N-diisopropylethylamine in 200 mL of dimethylsulfoxide (DMSO) was stirred for about 3 days. The reaction was quenched by pouring the reaction mixture onto 400 mL of dilute, cold sodium hydroxide. The resultant solution was extracted one time with 300 mL of ethyl acetate. An emulsion formed, which was broken up by warming it to about 35° C. The organic layer was separated and concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 40:1 methylene chloride:methanol as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 9.12 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe reaction was quenched
  2. additionby pouring the reaction mixture onto 400 mL
  3. additionof dilute
  4. extractionThe resultant solution was extracted one time with 300 mL of ethyl acetate
  5. customAn emulsion formed
  6. customThe organic layer was separated
  7. concentrationconcentrated under reduced pressure to a residue
  8. customThe residue was purified with column chromatography on silica gel using 40:1 methylene chloride
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-400147d6f459463cb9a4695ad0a6af5f
Source dataset
uspto-grants-2012_02
Patent number
US08119563B2

Reaction notes

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