Hydrochloric Acid → HCID 178511720, compound

HRID 271341Notes

Reaction equation

HRID 271341 reaction equation
[F:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25])[CH2:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11]C(=O)OC(C)(C)C)[CH2:7][CH2:6]1.Cl>O1CCOCC1>[F:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25])[CH2:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178454071HCID 178454071, compound

Product 1

HCID 178511720HCID 178511720, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1 g of tert-butyl {trans-4-[2-fluoro-2-(2-fluorophenyl)ethoxy]-cyclohexyl}carbamate an 10 mL of 4N HCl in dioxane was stirred at room temperature for 3 h then concentrated to dryness under reduced pressure. The white crystalline hydrochloride salt could be converted into the free base by partitioning between 25 mL of 3N sodium hydroxide and 3×25 mL portions of chloroform. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Further drying under vacuum gave 0.72 g of product as an oil which crystallized on standing: MS (m+1)=256.4; 1H NMR (400 MHz, CDCl3) 7.45 (m, 1H), 7.3 (m, 1H), 7.17 (m, 1H), 7.04 (m, 1H), 5.85 (dd, JHF=47 Hz, 1H), 3.75 (m, 2H), 3.3 (m, 1H), 2.7 (m, 1H), 2.02 (m, 2H), 1.85 (m, 2H), 1.3 (m, 2H), 1.05 (m, 2H).

Workup

  1. concentrationthen concentrated to dryness under reduced pressure
  2. customby partitioning between 25 mL of 3N sodium hydroxide and 3×25 mL portions of chloroform
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customFurther drying under vacuum

Sources & evidence

ORD record
ord-53573a5e4a2c41e2aaaae6fcc669922a
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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