Hydrochloric Acid → HCID 86753880, compound

HRID 1418370Notes

Reaction equation

HRID 1418370 reaction equation
[CH2:1]1[O:22][C:4]([O:20]C)([C:5]2[CH:10]=[CH:9][C:8]([C:11]([N:13]3[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]3)=[O:12])=[CH:7][CH:6]=2)[O:3][CH2:2]1.O.[OH-].[Li+].Cl>C1COCC1.O>[CH2:2]1[O:3][C:4]([OH:20])([C:5]2[CH:10]=[CH:9][C:8]([C:11]([N:13]3[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]3)=[O:12])=[CH:7][CH:6]=2)[O:22][CH2:1]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 131721185HCID 131721185, compound

Product 1

HCID 86753880HCID 86753880, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of methyl 4-(4-oxopiperidinocarbonyl)benzoate ethylene ketal (1.5 g, 4.9 mmol) and lithium hydroxide monohydrate (309 mg, 7.4 mmol) in THF/water (1:1) (50 ml) was stirred for 18 h, then acidified with dilute HCl. The product was extracted into ethyl acetate, and the extracts dried over sodium sulphate and concentrated to leave a white solid (1.4g), MS (+CI) 292 ([M+H]+), 1H NMR (CDCl3) 8.10 (2H, d, J 8.2 Hz), 7.45 (2H, d, J 8.3 Hz), 3.99 (4H, s), 3.86 (2H, br. s), 3.44 (2H, br. s), 1.81 (2H, br. s), 1.65 (2H, br. s)

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. dry with materialthe extracts dried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5fa1c9e2a23b469ab952a3f96b6215a7
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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