Hydrochloric Acid → HCID 66921928, compound

HRID 1363016Notes

Reaction equation

HRID 1363016 reaction equation
CC([N:5]([CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19]2[CH:20]=[C:21]([CH2:29][CH2:30][CH2:31][CH3:32])[CH:22]=[C:23]3[C:28]=2[N:27]=[CH:26][CH:25]=[CH:24]3)[CH2:14][CH2:13]1)C(=O)[O-])(C)C.Cl>O1CCOCC1>[CH2:29]([C:21]1[CH:22]=[C:23]2[C:28](=[C:19]([O:18][CH:15]3[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][NH2:5])[CH2:13][CH2:14]3)[CH:20]=1)[N:27]=[CH:26][CH:25]=[CH:24]2)[CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86635258HCID 86635258, compound2×

Product 1

HCID 66921928HCID 66921928, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl(3-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}propyl)carbamate (for example, as prepared for Intermediate 31) (493 mg, 1.12 mmol) was treated with a solution of hydrogen chloride in dioxane (4 M, 10 ml), and stirred under nitrogen overnight at room temperature. The mixture was concentrated in vacuo. The residue was dissolved in methanol, and applied to a SCX-2 ion exchange cartridge (10 g) which had been preconditioned with methanol. The cartridge was washed with methanol (100 ml), and then eluted with 10% aqueous 0.88 s.g. ammonia in methanol (100 ml). The relevant basic fractions were concentrated in vacuo to give the title compound (292 mg, 76%). LCMS RT=1.92 min, ES+ve m/z 342 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in methanol
  3. washThe cartridge was washed with methanol (100 ml)
  4. washeluted with 10% aqueous 0.88 s
  5. concentrationThe relevant basic fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-62764a71a8b3460f8c9f29e4dd334147
Source dataset
uspto-grants-2011_02
Patent number
US07884114B2

Reaction notes

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