Benzyl Bromide → HCID 49766299, compound

HRID 519306Notes

Reaction equation

HRID 519306 reaction equation
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][NH:4][CH2:3][CH:2]1[C:7]([O:9][CH3:10])=[O:8].[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=1.C(N(CC)CC)C>C(#N)C>[CH2:24]([N:4]1[CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1)[C:21]1[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 27568181-(1,1-Dimethylethyl) 2-methyl 1,2-piperazinedicarboxylate

Product 1

HCID 49766299HCID 49766299, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
71 °C

Procedure

To a dry 100 ml one necked round bottom flask equipped with a stirring bar was added 1-tert-butyl 2-methyl piperazine-1,2-dicarboxylate (5 g, 20.5 mmol) under N2 (FIG. 1). Anhydrous acetonitrile (60 mL) was added followed by the additions of BnBr (2.7 mL, 22.5 mmol) and triethylamine (8.5 ml, 61.5 mmol). A condenser was then put on to the flask and the reaction mixture was heated at 71° C. for 45 minutes. The reaction mixture was allowed to come to room temperature and concentrated under reduced pressure. It was then diluted with dichloromethane and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude compound was purified with flash column (PE:EA=8:1) to yield 4.5 g (66%) of 111a. MS: [M+H]+: 335

Workup

  1. customA condenser was then put on to the flask
  2. customto come to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionIt was then diluted with dichloromethane
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude compound was purified with flash column (PE:EA=8:1)

Sources & evidence

ORD record
ord-e68ffecc157647bfa26fe02a51ffbc25
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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