Hydrogen Bromide → HCID 86750085, compound

HRID 1081532Notes

Reaction equation

HRID 1081532 reaction equation
[OH:1][CH:2]1[CH2:7][CH:6]([CH2:8][NH2:9])[NH:5][CH:4]([CH2:10][NH2:11])[CH2:3]1.[Li+].[OH-].Br[CH2:15][C:16]([OH:18])=[O:17].Br>O>[C:16]([OH:18])(=[O:17])[CH3:15].[C:16]([OH:18])(=[O:17])[CH3:15].[C:16]([OH:18])(=[O:17])[CH3:15].[C:16]([OH:18])(=[O:17])[CH3:15].[C:16]([OH:18])(=[O:17])[CH3:15].[OH:1][CH:2]1[CH2:7][CH:6]([CH2:8][NH2:9])[NH:5][CH:4]([CH2:10][NH2:11])[CH2:3]1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 3939Lithium Hydroxide3×HCID 6227Bromoacetic AcidHCID 23362653HCID 23362653, compound

Product 1

HCID 86750085HCID 86750085, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

4-Hydroxy-2,6-piperidinedimethaneamine (10 mmol) is dissolved in water (10 ml). The pH is adjusted to 10 with 4M LiOH, and a solution of bromoacetic acid (55 mmol) and LiOH (55 mmol) in water (10 ml) is gradually added to the stirred mixture at ambient temperature. The temperature is gradually increased to 85° C. during 4 hours while the pH is kept in the alkaline range (8 to 10) with aqueous LiOH. The solution is allowed to cool to ambient temperature, neutralised with conc. hydrobromic acid, loaded on a strong cation exchanger (AG 5Wx4) and eluted with 6M aqueous ammonia. After evaporation down, the crude product is dissolved in water and lyophilised to yield the title compound.

Workup

  1. temperatureto cool to ambient temperature
  2. washeluted with 6M aqueous ammonia
  3. customAfter evaporation down
  4. dissolutionthe crude product is dissolved in water

Sources & evidence

ORD record
ord-e69453459d3d4f188c1d23165312afa0
Source dataset
uspto-grants-1996_12
Patent number
US05587144

Reaction notes

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