Hydrochloric Acid → HCID 23112232, compound

HRID 2264348Notes

Reaction equation

HRID 2264348 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[N:9]1([CH2:15][C:16]2[CH:17]=[C:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=[CH:20][C:21]=2[C:22](O)=[O:23])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[Cl-:31].[Na+].C(N=C=NCCCN(C)C)C.Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CN(C=O)C>[ClH:31].[OH:8][C:4]1[CH:3]=[C:2]([NH:1][C:22]([C:21]2[CH:20]=[CH:19][C:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:17][C:16]=2[CH2:15][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:23])[CH:7]=[CH:6][CH:5]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 115683-AminophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516892Sodium BicarbonateHCID 23112221HCID 23112221, compound

Product 1

HCID 23112232HCID 23112232, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 227 mg of 3-aminophenol, 3-(piperidin-1-ylmethyl)biphenyl-4-carboxylic acid (2.08 mmol), and sodium chloride was suspended into 7 ml of DMF and then 599 mg of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide was added thereto at room temperature, followed by 10 hours of stirring. Ethyl acetate and a 1M aqueous hydrochloric acid solution were added to the reaction solution and sodium hydrogen carbonate was added to the aqueous layer obtained by an operation of separation until the aqueous layer was rendered basic. Ethyl acetate was added to the aqueous layer and an operation of separation was conducted. The resulting organic layer was dried over anhydrous magnesium sulfate and then the solvent was removed by evaporation. The obtained white solid was dissolved in ethanol and a 4M ethyl acetate solution of hydrochloric acid was added thereto, followed by removal of the solvent by evaporation. Ethanol and water were added to the obtained reside and crystallization was effected to obtain 436 mg of N-(3-hydroxyphenyl)-3-(piperidin-1-ylmethyl)biphenyl-4-carboxamide hydrochloride as a white powder.

Workup

  1. additionwas added to the aqueous layer
  2. customobtained by an operation of separation until the aqueous layer
  3. customan operation of separation
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation
  6. dissolutionThe obtained white solid was dissolved in ethanol
  7. additiona 4M ethyl acetate solution of hydrochloric acid was added
  8. customfollowed by removal of the solvent by evaporation
  9. additionEthanol and water were added to the obtained reside and crystallization

Sources & evidence

ORD record
ord-b67d34a3251844eda5034004810f8366
Source dataset
uspto-grants-2010_12
Patent number
US07855198B2

Reaction notes

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