Acetic Acid → 1-{4-[5-(3-Chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}4-methyl piperidine-4-carboxylic acid

HRID 1777359Notes

Reaction equation

HRID 1777359 reaction equation
[OH-].[Na+].[OH-].[K+].C([O:7][C:8]([C:10]1([CH3:41])[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][C:31]([CH:34]5[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]5)=[C:30]([Cl:40])[CH:29]=4)[O:25][N:24]=3)=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=[O:9])C.C(O)(=O)C>O.O1CCCC1.C(O)C>[Cl:40][C:30]1[CH:29]=[C:28]([C:26]2[O:25][N:24]=[C:23]([C:20]3[CH:19]=[CH:18][C:17]([CH2:16][N:13]4[CH2:12][CH2:11][C:10]([CH3:41])([C:8]([OH:9])=[O:7])[CH2:15][CH2:14]4)=[CH:22][CH:21]=3)[N:27]=2)[CH:33]=[CH:32][C:31]=1[CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 708731974-Methyl-1-{4-[5-(3-chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 665749171-{4-[5-(3-Chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}4-methyl piperidine-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of sodium hydroxide (0.1 g, 0.0023 mol) and potassium hydroxide (85% assay, 0.13 g, 0.0020 mol) in demineralized water (2 mL) is added to a solution of 4-methyl-1-{4-[5-(3-chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}piperidine-4-carboxylic acid ethyl ester (0.3 g, 0.00057 mol) in tetrahydrofuran and ethanol (14 mL, 1:1). The reaction mixture is heated under reflux (80° C.) for 2 hrs. It is then concentrated under reduced pressure to give a crude residue which is dissolved in demineralized water (10 mL) and acidified to pH˜4-5 with 20% aqueous acetic acid solution. The resultant solid is filtered, dried and washed with acetone (2×10 mL). Solid is dried under vacuum to get 1-{4-[5-(3-chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}4-methyl piperidine-4-carboxylic acid.

Workup

  1. temperatureThe reaction mixture is heated
  2. concentrationIt is then concentrated under reduced pressure
  3. customto give a crude residue which
  4. filtrationThe resultant solid is filtered
  5. customdried
  6. washwashed with acetone (2×10 mL)
  7. customSolid is dried under vacuum

Sources & evidence

ORD record
ord-bda3a17043164fb080bcb7c957407cad
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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