Sodium Hydroxide → HCID 54043458, compound

HRID 442705Notes

Reaction equation

HRID 442705 reaction equation
[NH2:1]OS(O)(=O)=O.[OH:7][CH:8]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[OH-].[Na+]>O1CCCC1.O>[NH2:1][N:13]1[CH2:14][CH2:15][N:10]([CH2:9][CH:8]([OH:7])[CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 76284hydroxylamine-O-sulfonic acidHCID 544718361-[2'-Hydroxy-3'-octadecyloxypropyl]-piperazine

Product 1

HCID 54043458HCID 54043458, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent2×

Procedure

A solution of hydroxylamine-O-sulfonic acid (0.17 g, 1.5 mmol) in 1:1 tetrahydrofuran-water (10 mL) is added dropwise to a mixture of 1-[2'-hydroxy-3'-octadecyloxypropyl]-piperazine (3.0 g, 7.3 mmol) and sodium hydroxide (0.29 g) in 1:1 tetrahydrofuran-water (30 mL) at 15° C. over a 30 minute period under a nitrogen atmosphere. The resultant mixture is stirred at 15° C. for 2 hours. Three additional portions of NaOH (0.29 g each) are then added to the mixture. The reaction mixture is extracted with dichloromethane, dried over NaOH, concentrated and chromatographed to afford 1-N-Amino-4-N-[2'-hydroxy-3'-octadecyloxypropyl]-piperazine.

Workup

  1. extractionThe reaction mixture is extracted with dichloromethane
  2. dry with materialdried over NaOH
  3. concentrationconcentrated
  4. customchromatographed

Sources & evidence

ORD record
ord-30ba5b7c687545f087f3dca500a85ce1
Source dataset
uspto-grants-1999_04
Patent number
US05891881

Reaction notes

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