Hydrochloric Acid → HCID 67054286, compound

HRID 2406229Notes

Reaction equation

HRID 2406229 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:24][CH2:23][C:18]3(OCC[O:19]3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:16][CH2:17][C:18](=[O:19])[CH2:23][CH2:24]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67054497HCID 67054497, compound

Product 1

HCID 67054286HCID 67054286, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

8-((4′-Chlorobiphenyl-2-yl)methyl)-1,4-dioxa-8-azaspiro[4.5]decane (4.73 g, 13.76 mmol) was dissolved in dioxane (50 mL) and water (30 mL). Hydrochloric acid (37%, 14.3 mL, 174 mmol) was added, and the reaction was heated to 85° C. for 26 hours. After cooling to room temperature, the volatiles are removed in vacuo. The remaining aqueous phase is basified to pH ˜9 with 2M NaOH, and then extracted with CH2Cl2. The organic layers are dried over MgSO4 and concentrated to afford the title compound (4.13 g, 100% yield). MS (ESI) m/e (M+H)+: 300.4

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe volatiles are removed in vacuo
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layers are dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8a08b1a1fec74feeb17a326be7da2af4
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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