1,3-Dibromopropane → tert-Butyl 4-(3-bromopropyl)piperazine-1-carboxylate

HRID 1986160Notes

Reaction equation

HRID 1986160 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:4][CH2:3][CH2:2][Br:1])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

7

Reactant 4

HCID 80011,3-DibromopropaneHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 15946517tert-Butyl 4-(3-bromopropyl)piperazine-1-carboxylateYield 70.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1,3-Dibromopropane (6.78 mL, 66.8 mmol) is added to a stirred solution of piperazine-1-carboxylic acid tert-butyl ester (4.15 g, 22.2 mmol) and diisopropylethylamine (7.73 mL, 44.4 mmol) in anhydrous 1,4-dioxane (40 mL). The resultant mixture is heated in an oil bath at 90° C. for 20 hours. At ambient temperature ethyl acetate (160 mL) and half-saturated aqueous sodium bicarbonate (NaHCO3) (120 mL) are added to the mixture. The organic layer is separated, dried over magnesium sulfate, filtered, and concentrated. The crude oil is subjected to chromatography on silica gel and eluted with 2 M NH3/MeOH in dichloromethane 0-3% to provide the title compound as a dark oil (4.80 g, 70% yield).

Workup

  1. customThe organic layer is separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluted with 2 M NH3/MeOH in dichloromethane 0-3%

Sources & evidence

ORD record
ord-f59a4566692a4311826e44e1ce266616
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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