Succinic anhydride → N-(1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)succinamic Acid

HRID 1756840Notes

Reaction equation

HRID 1756840 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[NH2:8][CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:11]([CH3:25])([CH3:24])[CH2:10]1>CC(C)=O>[CH:18]1([O:17][N:12]2[C:11]([CH3:24])([CH3:25])[CH2:10][CH:9]([NH:8][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])[CH2:14][C:13]2([CH3:16])[CH3:15])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 222779844-Amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 23372131N-(1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)succinamic Acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 1.0 gram (10.0 mmol) of succinic anhydride in 25 ml of acetone is added to a solution of 2.64 gram (10.0 mmol) of 4-amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine (as prepared in Example 6B) in 10 ml of acetone. The reaction mixture is stirred for sixteen hours at room temperature and then concentrated to form a white solid. Purification by flash chromatography (silica gel; 9:1 ethyl acetate:ethanol) and recrystallization from heptane:ethyl acetate affords the title compound as a white solid melting at 136°-138° C.

Workup

  1. concentrationconcentrated
  2. customto form a white solid
  3. customPurification
  4. customby flash chromatography (silica gel; 9:1 ethyl acetate:ethanol) and recrystallization from heptane

Sources & evidence

ORD record
ord-12a4754f85554826aba082a158ace636
Source dataset
uspto-grants-1995_08
Patent number
US05442071

Reaction notes

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