Water → 4-(4-Bromobenzyl)piperazine, N1-BOC protected

HRID 590618Notes

Reaction equation

HRID 590618 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[C:10]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:20]2[CH2:19][CH2:18][N:17]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:22][CH2:21]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 27955194-(4-Bromobenzyl)piperazine, N1-BOC protected

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-bromobenzyl bromide (5 g, 20 mmol) and N-Boc piperazine (4.47 g, 24 mmol) in DMF (25 mL), K2CO3 (5.52 g, 40 mmol) was added and the reaction mixture was stirred for 16 h at room temperature. After completion of reaction (monitored by TLC), the reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (30 mL×3). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give crude product, V-1-I. This compound was used for next step without purification.

Workup

  1. additionwas added
  2. customAfter completion of reaction (monitored by TLC)
  3. extractionextracted with ethyl acetate (30 mL×3)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give crude product, V-1-I
  9. customThis compound was used for next step without purification

Sources & evidence

ORD record
ord-e3ebb349442a4dd5aa70e6b1b19bfef6
Source dataset
uspto-grants-2016_01
Patent number
US09233983B2

Reaction notes

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