Hydrochloric Acid → HCID 22240400, compound

HRID 890519Notes

Reaction equation

HRID 890519 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2.BrCCCCCC(Cl)=O.Cl>O1CCOCC1>[NH:14]1[C:15]2[C:11](=[CH:10][C:9]([N:3]3[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:2]3=[O:1])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 898486-Bromohexanoyl chlorideHCID 22240459HCID 22240459, compound

Product 1

HCID 22240400HCID 22240400, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Part A. To tert-butyl 5-(2-oxohexahydro-1H-azepin-1-yl)-1-indolinecarboxylate (140 mg, 0.42 mmol) that had been prepared as in Part C of Example 15 using 6-bromohexanoyl chloride instead of 5-bromovaleryl chloride was added 10 mL of 4.0 M HCl in dioxane. The resulting solution was maintained at rt under N2 for 2 h and was then concentrated. The resulting residue was dissolved in 25 mL of EtOAc, and the organic layer was washed with saturated aqueous NaHCO3. The aqueous layer was washed with EtOAc (2×50 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to afford 1-(2,3-dihydro-1H-indol-5-yl)hexahydro-2H-azepin-2-one (96 mg, 100%) as a brown oil. LC/MS (ESI+): 231.2 (M+H)+. 1H NMR (CDCl3) δ 6.9 (s, 1H), 6.79 (d, 1H), 6.76 (d, 1H), 3.98 (br s, 1H), 3.66 (br m, 2H), 3.52 (t, 2H), 3.01 (t, 2H), 2.65 (br s, 2H), 1.78 (br s, 6H).

Workup

  1. concentrationwas then concentrated
  2. dissolutionThe resulting residue was dissolved in 25 mL of EtOAc
  3. washthe organic layer was washed with saturated aqueous NaHCO3
  4. washThe aqueous layer was washed with EtOAc (2×50 mL)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ee268c51dea0456da6696433ff6c6fbc
Source dataset
uspto-grants-2006_02
Patent number
US06995172B2

Reaction notes

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