Potassium Iodide → Tert-butyl[4-(2-methyl-2-oxiranylmethyl)piperazin-1-yl]carbamate

HRID 856132Notes

Reaction equation

HRID 856132 reaction equation
C1(C)C=CC(S(O[CH2:11][C:12]2([CH3:15])[CH2:14][O:13]2)(=O)=O)=CC=1.[N:17]1([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)CC)C.[I-].[K+]>CN(C=O)C.O>[C:26]([O:25][C:24](=[O:30])[NH:23][N:17]1[CH2:22][CH2:21][N:20]([CH2:11][C:12]2([CH3:15])[CH2:14][O:13]2)[CH2:19][CH2:18]1)([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 142371942-Methyloxiran-2-ylmethyl paratoluenesulfonateHCID 21701658tert-Butyl piperazin-1-ylcarbamate

Product 1

HCID 23081164Tert-butyl[4-(2-methyl-2-oxiranylmethyl)piperazin-1-yl]carbamateYield 51.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (2-methyl-2-oxiranylmethyl) toluene-4-sufonate (9.75 g, 40.3 mmol), tert-butyl piperazin-1-yl-carbamate (6.75 g, 33.5 mmol) prepared in Reference Example 36, triethylamine (7 ml, 50.3 mmol) and potassium iodide (6.68 g, 33.5 mmol) in DMF (70 ml) was stirred at room temperature overnight. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water and brine, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/acetone=4/1) to afford tert-butyl[4-(2-methyl-2-oxiranylmethyl)piperazin-1-yl]carbamate (4.66 g, yield 51%) as a colorless crystalline powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/acetone=4/1)

Sources & evidence

ORD record
ord-22d6755f544d4a72960a99d739fd7135
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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