HCl butanone → HCID 67152368, compound

HRID 1677853Notes

Reaction equation

HRID 1677853 reaction equation
O1[C:5]2([CH2:9][CH2:8][N:7]([C@H:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]3[O:16][CH2:17][CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:6]2)[O:4]CC1.[ClH:31].CC(=O)CC>>[ClH:31].[O:4]=[C:5]1[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[O:16][CH2:17][CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:6]1

Participants

3

Reactant 2

HCID 12200355HCl butanoneHCID 86761395(1S,2S)-2-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)-1-(2,2-diphenylethoxy)cyclohexane

Product 1

HCID 67152368HCID 67152368, compoundYield 80%

Procedure

A mixture of (1R,2R)/(1S,2S)-2-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)-1-(2,2-diphenylethoxy)cyclohexane (1.55 g, 3.8 mmol) in 6M HCl-butanone (1:4, v/v, 50 mL) was refluxed for 2 hours. The butanone was evaporated in vacuo and the residue was taken up with water (50 mL). The aqueous solution was extracted with diethyl ether (2×50 mL); the aqueous layer was collected and extracted with dichloromethane (2×50 mL). The combined dichloromethane extracts were dried over sodium sulfate and concentrated in vacuo to yield the crude title compound. The product was crystallized by triturating in diethyl ether and reprecipitated from a mixture of dichloromethane-diethyl ether to yield 1.21 g (80% yield) of the title compound, having the elemental analysis indicated in Table 1.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe butanone was evaporated in vacuo
  3. extractionThe aqueous solution was extracted with diethyl ether (2×50 mL)
  4. customthe aqueous layer was collected
  5. extractionextracted with dichloromethane (2×50 mL)
  6. dry with materialThe combined dichloromethane extracts were dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto yield the crude title compound
  9. customThe product was crystallized
  10. customby triturating in diethyl ether
  11. customreprecipitated from a mixture of dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-ccb26d698f0f409db49e525b6967c34f
Source dataset
uspto-grants-2011_08
Patent number
US08008342B2

Reaction notes

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