Hydrochloric Acid → HCID 59662178, compound

HRID 409565Notes

Reaction equation

HRID 409565 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][CH2:20][C:19]2=[O:28])[CH2:12][CH2:11]1.O.[OH-].[Li+].Cl>C1COCC1>[O:28]=[C:19]1[N:18]([CH2:17][CH2:16][N:13]2[CH2:14][CH2:15][CH:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:29])=[O:2])[CH2:11][CH2:12]2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[O:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 24803495HCID 24803495, compound

Product 1

HCID 59662178HCID 59662178, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

2-{1-[2-(3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethyl]-piperidin-4-yl}-benzoic acid methyl ester Compound 93 (1.2 g, 3.0 mmol) was dissolved in THF (10 mL) and treated with lithium hydroxide monohydrate (864 mg, 21 mmol). The reaction mixture was heated to 40° C. for 24 hrs, cooled to rt, adjusted to pH 3 with 1N HCl, and concentrated in vacuo. Purification by Gilson HPLC (elution with 10 to 90 gradient of H2O 0.2% TFA buffer/acetonitrile with 0.1% TFA buffer) afforded Compound 3-1 as a white solid (1.45 g, 2.93 mmol, 98%). 1H NMR (300 MHz, CDCl3) δ 8.71 (d, J=5 Hz, 1H), 7.92 (m, 1H), 7.59-7.43 (m, 2H), 7.32-7.22 (m, 1H), 7.14-6.89 (m, 3H), 4.62 (s, 2H), 3.97-3.68 (m, 2H), 3.45-2.94 (m, 4H), 2.71-2.33 (m, 3H), 2.13-1.96 (m, 2H), 1.80-1.65 (m, 2H); MS (ES+) m/z 381.1 (M+1).

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated in vacuo
  3. customPurification
  4. washby Gilson HPLC (elution with 10 to 90 gradient of H2O 0.2% TFA buffer/acetonitrile with 0.1% TFA buffer)

Sources & evidence

ORD record
ord-6f05c2303a2f439793707c95646bb61e
Source dataset
uspto-grants-2014_06
Patent number
US08759342B2

Reaction notes

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