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

HRID 1885674Notes

Reaction equation

HRID 1885674 reaction equation
[CH2:1]([NH:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]([CH3:22])([CH3:21])[CH2:7]1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:30]1(=[O:36])[O:35][C:33](=[O:34])[CH2:32][CH2:31]1>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:5]([CH:6]1[CH2:7][C:8]([CH3:21])([CH3:22])[N:9]([O:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[C:10]([CH3:13])([CH3:12])[CH2:11]1)[C:30](=[O:36])[CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 211821294-Butylamino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 23372132N-Butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-succinamic AcidYield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 10.2 grams (33 mmol) of 4-n-butylamino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine (prepared in Example 8), 3.3 grams (33 mmol) of triethylamine, and 30 ml of tetrahydrofuran is added to a solution of 3.0 grams (30 mmol) of succinic anhydride in 20 ml of tetrahydrofuran over a 5-minute period. The reaction mixture is stirred for six hours and then diluted with ethyl acetate (200 ml). The organic solution is washed with 1N hydrochloric acid (2×50 ml), washed with water (50 ml), washed with saturated sodium chloride solution (50 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give an oil which crystallizes on standing. Recrystallization from heptane affords 5.6 grams (46% yield) of the title compound as a white solid melting at 110°-113° C.

Workup

  1. washThe organic solution is washed with 1N hydrochloric acid (2×50 ml)
  2. washwashed with water (50 ml)
  3. washwashed with saturated sodium chloride solution (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil which
  7. customcrystallizes
  8. customRecrystallization from heptane

Sources & evidence

ORD record
ord-c51dbe79341a42a7a230a87f50b36085
Source dataset
uspto-grants-1992_09
Patent number
US05145893

Reaction notes

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