Hydrochloric Acid → HCID 69008872, compound

HRID 2175449Notes

Reaction equation

HRID 2175449 reaction equation
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)=[O:16])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Li+].Cl>CO.C1COCC1.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([NH:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=3)=[O:16])[CH2:12][CH2:13]2)=[CH:27][CH:28]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57951063HCID 57951063, compound

Product 1

HCID 69008872HCID 69008872, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl 4-(1-(4-cyanobenzyl)piperidin-4-ylcarbamoyl)benzoate (900 mg, 2.38 mmol) and lithium hydroxide (600 mg, 14.28 mmol) was added to MeOH/THF/H2O(2/1/1, 20 mL), and the mixture was stirred overnight, then acidified with 2M hydrochloric acid (10 mL) to pH 5. A white solid separated, and was collected by filtration and washed with water. The combined filtrate and washings were acidified by adding further 2M hydrochloric acid to pH 1 and the solution was extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried with magnesium sulphate and evaporated to give 4-(1-(4-cyanobenzyl)piperidin-4-ylcarbamoyl)benzoic acid (0.718 g, 83%). LCMS (m/z): 364 (MH+).

Workup

  1. customA white solid separated
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. additionby adding further 2M hydrochloric acid to pH 1
  5. extractionthe solution was extracted three times with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried with magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-7f56f94aeff94d3b9a0c3c8cacd6f2c8
Source dataset
uspto-grants-2015_06
Patent number
US09062052B2

Reaction notes

Loading…