Hydrochloric Acid → HCID 19426276, compound

HRID 742539Notes

Reaction equation

HRID 742539 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([OH:21])=[O:20])[CH2:14][CH2:13][N:12]([CH2:22][C:23]([OH:25])=[O:24])[CH2:11][CH2:10]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH-].[Na+].Br[CH2:29][C:30]([OH:32])=[O:31].Cl>O>[C:30]([CH2:29][N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][N:9]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([OH:21])=[O:20])[CH2:14][CH2:13][N:12]([CH2:22][C:23]([OH:25])=[O:24])[CH2:11][CH2:10]2)[CH2:2][CH2:3]1)([OH:32])=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 14798Sodium Hydroxide2×HCID 19426277HCID 19426277, compound

Product 1

HCID 19426276HCID 19426276, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(2-piperazinoethyl)-4,7-bis-(carboxymethyl)-1,4,7-triazacyclononane (10.7 g, 0.03 mol) in 100 mL of deionized water is adjusted to pH 10 with 1N sodium hydroxide solution. Then bromoacetic acid (4.2 g, 0.03 mol) is added and the solution is heated at 50 C. for 15 hours, keeping the pH between 9 and 10 with 1N sodium hydroxide. After cooling the reaction mixture to 25 C., the pH is adjusted to 4 with 1N hydrochloric acid. The solvent is removed under reduced pressure to give 1-[2-(4-carboxymethylpiperazino)ethyl]-4,7-bis-(carboxymethyl)-1,4,7-triazacyclonane.

Workup

  1. temperaturethe solution is heated at 50 C
  2. temperatureAfter cooling the reaction mixture to 25 C
  3. customThe solvent is removed under reduced pressure
  4. customto give 1-[2-(4-carboxymethylpiperazino)ethyl]-4,7-bis-(carboxymethyl)-1,4,7-triazacyclonane

Sources & evidence

ORD record
ord-9630f40a972a4436a3b5ef4901ec7328
Source dataset
uspto-grants-1996_09
Patent number
US05554749

Reaction notes

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