Hydrochloric Acid → HCID 58046560, compound

HRID 706356Notes

Reaction equation

HRID 706356 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58046571HCID 58046571, compound

Product 1

HCID 58046560HCID 58046560, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-[trans-3-(4-Chlorophenyl)allyl]-1,4-dioxa-8-azaspiro[4.5]decane (1.38 g) was dissolved in methanol (40 ml) and 6 N hydrochloric acid (120 ml) was added. The mixture was heated to reflux for 4 h. The mixture cooled and was basified to pH 14 with solid sodium hydroxide pellets (CARE! Exotherm), the solution becoming opaque. The aqueous was extracted three times with ether. The organics were washed with brine, dried over anhydrous MgSO4 and evaporated to give 1.17 g (100%) of the desired ketone 1H NMR (400 MHz, CDCl3) 2.38 (m, 4H), 2.70 (m, 4H), 3.15 (d, J=5 Hz, 2H), 3.96 (s, 4H), 6.17 (dt, J=12 & 5 Hz, 1H), 6.40 (d, J=12 Hz, 1H), 7.20 (m, 4H). MS (ES+) 250/252 M+H+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. temperatureThe mixture cooled
  4. extractionThe aqueous was extracted three times with ether
  5. washThe organics were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-86eabd252a90479f95496e3335cb752a
Source dataset
uspto-grants-2015_11
Patent number
US09174987B2

Reaction notes

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