Hydrogen Bromide → 1-Tert-butylpiperazine dihydrobromide

HRID 988697Notes

Reaction equation

HRID 988697 reaction equation
[C:1]([NH:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11]OC1=O)([CH3:4])([CH3:3])[CH3:2].[BrH:14].ClCCl>C(O)(=O)C>[BrH:14].[BrH:14].[C:1]([N:5]1[CH2:6][CH2:7][NH:8][CH2:12][CH2:11]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 12268380HCID 12268380, compound

Product 1

HCID 219063541-Tert-butylpiperazine dihydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To crude 3-[2-(tert-butylamino)ethyl]oxazolidin-2-one (1.18 g, 6.33 mmol) was added acetic acid (8.8 mL) and then 45% hydrobromic acid in acetic acid (19.5 mL). The reaction solution was stirred at room temperature for 3 d, poured into dichloromethane (250 mL), and filtered to give 1.87 g of a brown solid. The solid was heated at reflux in n-butanol for 2 d and the reaction mixture concentrated in vacuo. The residual solid was slurried in 3:1 diethyl ether:dichloromethane and filtered. The filtered solid was heated in ethanol, cooled to room temperature, and filtered to give 0.57 g (30%) of a white solid.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-886c57bbc59c4a4eb83c88f7ebbf207f
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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