Tetrahydrofuran → Bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) Hydrazine-1,2-dicarboxylate

HRID 742614Notes

Reaction equation

HRID 742614 reaction equation
ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[CH2:13]([O:21][N:22]1[C:27]([CH3:29])([CH3:28])[CH2:26][CH:25]([OH:30])[CH2:24][C:23]1([CH3:32])[CH3:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O.[NH2:34][NH2:35].[C:36](=[O:39])([O-])[O-].[Na+].[Na+].[O:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1>O.C(N(CC)CC)C>[NH:34]([C:5]([O:6][CH:7]1[CH2:26][C:27]([CH3:29])([CH3:28])[N:22]([O:42][CH2:46][CH2:45][CH2:44][CH2:43][CH2:13][CH2:14][CH2:15][CH3:16])[C:23]([CH3:31])([CH3:32])[CH2:24]1)=[O:11])[NH:35][C:36]([O:30][CH:25]1[CH2:26][C:27]([CH3:29])([CH3:28])[N:22]([O:21][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:23]([CH3:31])([CH3:32])[CH2:24]1)=[O:39]

Participants

8

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 94429TriphosgeneHCID 113466831-Octyloxy-2,2,6,6-tetramethylpiperidin-4-ol

Product 1

HCID 15345986Bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) Hydrazine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 29.7 g of triphosgene in 120 mL of tetrahydrofuran (THF) is added a solution of 85.7 g of 1-octyloxy-2,2,6,6-tetramethylpiperidin-4-ol and 42.0 mL of triethylamine in 240 mL of THF over 4 hours at 5°-10° C., followed by 7.3 mL of hydrazine hydrate. After stirring the reaction mixture at room temperature for 18 hours, a solution of 71.0 g of sodium carbonate in 500 mL of water is added and the organic layer is removed, washed with water and dried over anhydrous magnesium sulfate. The dried solution is evaporated to afford 97.2 g of the title compound as an oil.

Workup

  1. customthe organic layer is removed
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe dried solution is evaporated

Sources & evidence

ORD record
ord-d5829c5eeb77472e9e7b62e4e6b15504
Source dataset
uspto-grants-1996_09
Patent number
US05554754

Reaction notes

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