Water → HCID 66868904, compound

HRID 1850822Notes

Reaction equation

HRID 1850822 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH2:25])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30].C(N(CC)CC)C.O>ClCCl>[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29]([NH:25][CH2:24][CH2:23][O:22][C:19]1[CH:20]=[C:21]2[C:16]([CH2:15][CH2:14][N:13]=[C:12]2[C:8]2([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:17][CH:18]=1)=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 66868651HCID 66868651, compound

Product 1

HCID 66868904HCID 66868904, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(1-(1-(4-chlorophenyl)cyclobutyl)-3,4-dihydroisoquinolin-7-yloxy)ethanamine (80.0 mg, 0.15 mmol), 2,4-dichloro-benzoyl chloride (44.3 mg, 0.21 mmol), and triethyl amine (48.6 mg, 0.48 mmol) were dissolved in dichloromethane (2 ml) and stirred for 14 h at RT. Water was added and the mixture was extracted with ethyl acetate. The organic layers were washed with water and saturated NaCl solution, dried with MgSO4, and the solvent was removed. The residue was purified by flash chromatography on silica gel using methylenchloride/MeOH 98:2→95:5 to give 2,4-dichloro-N-(2-{1-[1-(4-chloro-phenyl)-cyclobutyl]-3,4-dihydro-isoquinolin-7-yloxy}-ethyl)-benzamide as a colourless oil (85.0 mg, 0.16 mmol, 84%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layers were washed with water and saturated NaCl solution
  3. dry with materialdried with MgSO4
  4. customthe solvent was removed
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-a1bf71f75f9d404aa1f7108a9da51891
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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