Hydrochloric Acid → 84163-18-8

HRID 72852Notes

Reaction equation

HRID 72852 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12](C(=O)C)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.Cl>CCOCC>[ClH:1].[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66741568HCID 66741568, compound

Product 1

HCID 1307643184163-18-8Yield 157.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-[4-(6-Chloro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-ethanone (1.45 g, 5.3 mmol) was diluted with an aqueous solution of HCl 6N (13.8 mL, 16 mmol) and the mixture was refluxed overnight. After cooling, 2×20 mL of ether was added and the mixture extracted. A solution of NaOH was added to the aqueous phase until pH 11 and the mixture was extracted with ethyl acetate three times. The combined ethyl acetate fractions were dried and evaporated under reduced pressure to yield 1.14 g of a light brown solid (93%). MS (m/e): 236.9 (M+H+).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperatureAfter cooling
  3. extractionthe mixture extracted
  4. additionA solution of NaOH was added to the aqueous phase until pH 11
  5. extractionthe mixture was extracted with ethyl acetate three times
  6. dry with materialThe combined ethyl acetate fractions were dried
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3847695cde3349b787455f80e20b7ab5
Source dataset
uspto-grants-2014_09
Patent number
US08829029B2

Reaction notes

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