2-Bromobenzyl bromide → Tert-butyl 4-(2-bromobenzyl)piperazine-1-carboxylate

HRID 731555Notes

Reaction equation

HRID 731555 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[Br:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Br>C(#N)C>[Br:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 769652-Bromobenzyl bromideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 20754660Tert-butyl 4-(2-bromobenzyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl 1-piperazinecarboxylate (5.51 g, 29.623 mmol) in acetonitrile (60 mL) at 0° C. was treated with diisopropylethylamine and 2-bromobenzyl bromide (7.776 g, 31.105 mmol), warmed to room temperature, stirred for 2 hours, and concentrated. The residue was partitioned between ethyl acetate and aqueous NaHCO3. The aqueous layer was extracted with ethyl acetate and the combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was used directly in the next step without further purification.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and aqueous NaHCO3
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was used directly in the next step without further purification

Sources & evidence

ORD record
ord-9a796408c7324664a105b8aedfeab023
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

Loading…