Bromine → HCID 67388556, compound

HRID 908395Notes

Reaction equation

HRID 908395 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1>C(O)(=O)C>[Br:1][C:10]1[CH:9]=[CH:8][C:7]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]2)=[CH:6][C:5]=1[O:4][CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 63787796HCID 63787796, compound

Product 1

HCID 67388556HCID 67388556, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (0.715 ml) was added dropwise to tert-butyl 4-(3-methoxyphenyl)piperazine-1-carboxylate (3.4 g) dissolved in cold acetic acid (25 ml) under argon. The resulting solution was stirred at room temperature for 90 minutes. The reaction mixture was concentrated to dryness and diluted with ethyl acetate, dichloromethane and a saturated aqueous solution of sodium bicarbonate. The phases were stirred, separated and the organic phase was dried over magnesium sulfate and concentrated in the presence of silica gel. The crude product was purified by flash chromatography on silica gel eluting with 10 to 20% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford tert-butyl 4-(4-bromo-3-methoxy-phenyl)piperazine-1-carboxylate (1.770 g, 41.0%). NMR Spectrum: (CDCl3) 1.48 (s, 9H), 3.08-3.17 (m, 4H), 3.54-3.62 (m, 4H), 3.88 (s, 3H), 6.40 (dd, 1H), 6.47 (d, 1H), 7.37 (d, 1H)

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additiondiluted with ethyl acetate, dichloromethane
  3. stirringThe phases were stirred
  4. customseparated
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated in the presence of silica gel
  7. customThe crude product was purified by flash chromatography on silica gel eluting with 10 to 20% ethyl acetate in petroleum ether
  8. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-92b807f54acf4f428c9b85adaeee37d7
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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