Water → Ethyl 3-{1-(4-bromobenzoyl)-4-hydroxypiperidin-4-yl}alpha,alpha-dimethylphenoxyacetate

HRID 1734224Notes

Reaction equation

HRID 1734224 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[CH2:13][CH2:12][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3O)([OH:14])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-:25].[K+].[K+].O.Br[C:32]([CH3:39])([CH3:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:13][CH2:12][C:11]([C:15]3[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=3)[O:25][C:32]([CH3:39])([CH3:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])([OH:14])[CH2:10][CH2:9]2)=[O:7])=[CH:22][CH:23]=1

Participants

5

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 152946731-(4-Bromobenzoyl)-4-(2-hydroxyphenyl)-4-hydroxypiperidine

Product 1

HCID 22399364Ethyl 3-{1-(4-bromobenzoyl)-4-hydroxypiperidin-4-yl}alpha,alpha-dimethylphenoxyacetateYield 86.4%

Procedure

801 mg of {1-(4-bromobenzoyl)-4-(2-hydroxyphenyl)-4-hydroxypiperidine was stirred for 9 hours at the ambient temperature of 100° C. in the presence of 1.20 g (8.68 mmol) of potassium carbonate in 4.00 g (20.5 ml) of ethyl α-bromoisobutyrate. After completion of the reaction, The reaction mixture was cooled, and water was added thereto, followed by extraction with chloroform. Subsequently, the extract was dried over anhydrous sodium sulfate. Chloroform and the remained ethyl α-bromoisobutyrate was distilled off under reduced pressure to obtain 902 mg (86.4%) of ethyl 3-{1-(4-bromobenzoyl)-4-hydroxypiperidin-4-yl}α,α-dimethylphenoxyacetate.

Workup

  1. customAfter completion of the reaction
  2. temperatureThe reaction mixture was cooled
  3. extractionfollowed by extraction with chloroform
  4. dry with materialSubsequently, the extract was dried over anhydrous sodium sulfate
  5. distillationChloroform and the remained ethyl α-bromoisobutyrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1b13c5df5249460cb75e8a2f2a1eeae2
Source dataset
uspto-grants-1996_07
Patent number
US05532371

Reaction notes

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