Hydrochloric Acid → HCID 18617602, compound

HRID 1264240Notes

Reaction equation

HRID 1264240 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH-].[Na+].Cl>CO>[O:1]=[C:2]1[NH:7][CH2:6][CH:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 18617476HCID 18617476, compound

Product 1

HCID 18617602HCID 18617602, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-(6-oxo-piperidin-3-yl)-benzoate (320 mg, 1.30 mmol, reference example 66) is dissolved in MeOH (8 mL). To this solution is added 1 N NaOH (1.43 mL, 1.43 mmol) and the resulting solution stirred at room temperature for 1 hour. An additional portion of 1 N NaOH (2 mL) is added and the mixture allowed to stir at room temperature overnight (16 hours). 1 N HCl is added until pH 2-3 is reached. A precipitate formed and is filtered, washed with water and placed in a vacuum oven to dry overnight to afford the title compound (250 mg, 88%) as small white crystals (needles). 1H NMR (300 MHz, DMSO) δ 1.94 (m, 2H), 2.23 (m, 2H), 3.06 (m, 1H), 3.23 (m, 2H), 7.42 (d, J=8.3, 2H), 7.57 (bs, 1H), 7.87 (d, J=8.1, 2H); MS (Ion spray) m/z 220 (M+H)+.

Workup

  1. stirringto stir at room temperature overnight (16 hours)
  2. customA precipitate formed
  3. filtrationis filtered
  4. washwashed with water
  5. customto dry overnight

Sources & evidence

ORD record
ord-c62f37d8430d494f84cf10f44f5244a2
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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