Hydrochloric Acid → 2-(1,4'-Bipiperidin-1'-yl)benzo[d]oxazole-5-carboxylic acid

HRID 2041012Notes

Reaction equation

HRID 2041012 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3[O:14][C:15]4[CH:21]=[CH:20][C:19]([C:22]([O:24]C)=[O:23])=[CH:18][C:16]=4[N:17]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].CO.Cl>O1CCCC1.O>[N:1]1([CH:7]2[CH2:8][CH2:9][N:10]([C:13]3[O:14][C:15]4[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][C:16]=4[N:17]=3)[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 66905434HCID 66905434, compound

Product 1

HCID 669058032-(1,4'-Bipiperidin-1'-yl)benzo[d]oxazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 2-(1,4′-bipiperidin-1′-yl)benzo[d]oxazole-5-carboxylate (Example 94, 220 mg, 0.641 mmol) and potassium hydroxide were combined in a mixture of tetrahydrofuran, methanol, and water (9:1:1, 7 mL) and stirred at 40° C. overnight. The mixture was neutralized with concentrated hydrochloric acid, concentrated under reduced pressure, and triturated with chloroform to afford the title compound. MS (ESI+) m/z 330.2 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customtriturated with chloroform

Sources & evidence

ORD record
ord-4ca1837ed2c1422287d98e3f52933036
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

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