1,2-Dibromoethane → tert-Butyl 4-(2-bromoethyl)piperazine-1-carboxylate

HRID 588849Notes

Reaction equation

HRID 588849 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.[Br:14][CH2:15][CH2:16]Br.CCN(C(C)C)C(C)C>>[Br:14][CH2:15][CH2:16][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

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 15946441tert-Butyl 4-(2-bromoethyl)piperazine-1-carboxylateYield 36%

Conditions

Temperature
30 °C

Procedure

A mixture of tert-butyl piperazine-1-carboxylate (5.0 g, 26.9 mmol), 1,2-dibromoethane (25 mL), DIPEA (3.5 g, 26.9 mmol) was stirred at 30° C. under argon for 72 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (1-2% methanol/dichloroethane) to afford the desired product (2.8 g, 36% yield) as a solid. ESI-MS m/z: 293.1[M+1]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (1-2% methanol/dichloroethane)

Sources & evidence

ORD record
ord-2b9d0387338e4dc195525984ba4b5ef6
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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