Sodium Carbonate → tert-Butyl 4-(3-bromopropyl)piperazine-1-carboxylate

HRID 2079557Notes

Reaction equation

HRID 2079557 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35]O)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[Br:37]C(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][Br:37])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 162178001-Boc-4-(3-hydroxypropyl)piperazine

Product 1

HCID 15946517tert-Butyl 4-(3-bromopropyl)piperazine-1-carboxylateYield 65.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atmosphere, a solution of triphenylphosphine (0.94 g) in THF (4 ml) was added slowly to a mixture of 4-(3-hydroxy-propyl)-piperazine-1-carboxylic acid tert-butyl ester (0.80 g) and tetrabromomethane (1.19 g) in THF (15 ml). The mixture was stirred at room temperature for 16 hours, then ethyl acetate (100 ml) and a saturated solution of sodium carbonate (30 ml) were added and the organic layer was washed with brine, then dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent: Cyclohexane/Ethyl acetate 8/2) to afford 4-(3-bromo-propyl)-piperazine-1-carboxylic acid tert-butyl ester (0.66 g).

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed over silica gel (eluent: Cyclohexane/Ethyl acetate 8/2)

Sources & evidence

ORD record
ord-56a8eb1107bb4a9d937be37c8554fc6c
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

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