Sodium Chloride → HCID 23112209, compound

HRID 731961Notes

Reaction equation

HRID 731961 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[C:12]([C:14](O)=[O:15])[CH:11]=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[Na+].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>ClCCCl.O>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([NH:30][C:14]([C:12]2[CH:11]=[CH:10][C:9]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:13]=2)=[O:15])[CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 79724-MethylmorpholineHCID 108243-MethoxyanilineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23112265HCID 23112265, compound

Product 1

HCID 23112209HCID 23112209, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

Into 20 ml of 1,2-dichloroethane were suspended 500 mg of a mixture of 2-(piperidin-1-ylmethyl)biphenyl-4-carboxylic acid and 1.5 equivalents of sodium chloride, and then 174 mg of 3-methoxyaniline dissolved in 2 ml of 1,2-dichloroethane was added thereto. Under ice cooling, 694 mg of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate and 211 μl of N-methylmorpholine were added thereto, followed by 30 hours of stirring at room temperature. Water was added to the reaction solution and the organic layer was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, followed by removal of the solvent by evaporation. The obtained residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia) to obtain N-(3-methoxyphenyl)-2-(piperidin-1-ylmethyl)biphenyl-4-carboxamide. The compound was dissolved in 3 ml of ethyl acetate and then 1 ml of a 4M ethyl acetate solution of hydrochloric acid was added thereto. The solvent was removed by evaporation and crystallization was effected from ethanol to obtain 103 mg of N-(3-methoxyphenyl)-2-(piperidin-1-ylmethyl)biphenyl-4-carboxamide hydrochloride as a white powder.

Workup

  1. additionwas added
  2. extractionthe organic layer was extracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customfollowed by removal of the solvent by evaporation
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia)

Sources & evidence

ORD record
ord-4724e43a896a48ed99355e628f3ae785
Source dataset
uspto-grants-2009_09
Patent number
US07585878B2

Reaction notes

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