Sodium Hydroxide → HCID 66630380, compound

HRID 555375Notes

Reaction equation

HRID 555375 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([CH:19]3[CH2:21][CH2:20]3)=[O:18])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[CH:19]1([C:17]([N:14]2[CH2:13][CH2:12][CH:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:22])=[O:2])=[CH:9][CH:8]=3)[CH2:16][CH2:15]2)=[O:18])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66630438HCID 66630438, compound

Product 1

HCID 66630380HCID 66630380, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(1-cyclopropanecarbonyl-piperidin-4-yloxy)-benzoic acid methyl ester (0.75 g, 2.472 mmol), methanol (25 mL) and 1 N NaOH (10 mL) was stirred at room temperature for 16 hrs. The volatiles were evaporated in vacuo and the residue was redissolved in water (10 mL) and washed with EtOAc (2×5 mL). The aqueous phase was acidified to pH ˜1 with 1N HCl and extracted with EtOAc (2×10 mL), dried (MgSO4), filtered and evaporated affording 0.6 g 84%) of 4-(1-cyclopropanecarbonyl-piperidin-4-yloxy)-benzoic acid as a solid. 1H-NMR (400 MHz, CDCl3) δ 0.73-0.84 (m, 2H), 0.97-1.07 (m, 2H), 1.72-2.11 (m, 5H), 3.63-3.74 (m, 2H), 3.75-4.00 (m, 2H), 4.64-4.75 (m, 1H), 6.96 (d, 2H), 8.06 (d, 2H).

Workup

  1. customThe volatiles were evaporated in vacuo
  2. dissolutionthe residue was redissolved in water (10 mL)
  3. washwashed with EtOAc (2×5 mL)
  4. extractionextracted with EtOAc (2×10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4bd9fd41b96b4e4781f8cb34fafa2e45
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

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