4-Piperidinone, 3,5-dibromo-2,2,6,6-tetramethyl-, hydrobromide (1:1) → 2,2,5,5-Tetramethyl-3-pyrroline-3-carboxylic Acid (5-Hydroxy-2,2-dimethyl-1,3-dioxepan-6-yl)-amide

HRID 231070Notes

Reaction equation

HRID 231070 reaction equation
Br.Br[CH:3]1[C:8](=[O:9])[CH:7](Br)[C:6]([CH3:12])([CH3:11])[NH:5][C:4]1([CH3:14])[CH3:13].CC([O-])(C)C.[K+].[NH2:21][CH:22]1[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25][CH2:24][CH:23]1[OH:31]>C(O)(C)C>[OH:31][CH:23]1[CH:22]([NH:21][C:8]([C:7]2[C:6]([CH3:11])([CH3:12])[NH:5][C:4]([CH3:3])([CH3:13])[CH:14]=2)=[O:9])[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25][CH2:24]1

Participants

5

Reactant 3

HCID 892514-Piperidinone, 3,5-dibromo-2,2,6,6-tetramethyl-, hydrobromide (1:1)HCID 33874446-Amino-2,2-dimethyl-1,3-dioxepan-5-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 542048022,2,5,5-Tetramethyl-3-pyrroline-3-carboxylic Acid (5-Hydroxy-2,2-dimethyl-1,3-dioxepan-6-yl)-amide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Analogously to Example 7, 78.79 g (200 mmol) of 3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one hydrobromide, 69.34 g of potassium tert-butylate, and 35.47 g (220 mmol) of 6-amino-2,2-dimethyl-1,3-dioxepan-5-ol are reacted in 800 ml of isopropanol and then extracted with dichloromethane. Yield: 37.66 g (60.3% of theory) of 2,2,5,5-tetramethyl-3-pyrroline-3-carboxylic acid (5-hydroxy-2,2-dimethyl-1,3-dioxepan-6-yl)amide which, crystallized from diethyl ether/hexane, shows a melting point of 125°-127° C.

Workup

  1. extractionextracted with dichloromethane
  2. customYield: 37.66 g (60.3% of theory) of 2,2,5,5-tetramethyl-3-pyrroline-3-carboxylic acid (5-hydroxy-2,2-dimethyl-1,3-dioxepan-6-yl)amide which, crystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-c2577182005a46319ea49a89d9fd366e
Source dataset
uspto-grants-1989_07
Patent number
US04845090

Reaction notes

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