Sodium Hydroxide → HCID 10728458, compound

HRID 2168211Notes

Reaction equation

HRID 2168211 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14]C)=[O:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([OH:14])=[O:13])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10538587HCID 10538587, compound

Product 1

HCID 10728458HCID 10728458, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 3-{[2-(1-pyrrolidinyl)ethyl]oxy}benzoate D37 (1.6 g) and sodium hydroxide (708 mg, 18.2 mmol) in MeOH (50 ml) and water (10 ml) was refluxed for 18 hours. The reaction was concentrated and water added and acidified to pH3 with 2M HCl solution. The reaction was concentrated and was added MeOH and was filtered, concentrated to give a brown solid of desired product D38 in 1.5 g. LCMS [MH+] [email protected] min (5 min run)

Workup

  1. concentrationThe reaction was concentrated
  2. additionwater added
  3. concentrationThe reaction was concentrated
  4. additionwas added MeOH
  5. filtrationwas filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-afc8727f38cd4ff1ad94e38a9f0810cf
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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