Potassium Iodide → N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-phenylprop yl]-4-pyrrolidin-1-ylmethylbenzamide hydrochloride

HRID 548207Notes

Reaction equation

HRID 548207 reaction equation
[ClH:1].[F:2][C:3]([F:27])([F:26])[C:4]1[CH:5]=[C:6]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:7][O:8][CH2:9][CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:11][NH2:12].[CH2:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[CH3:29].CCN=C=N[CH2:40][CH2:41][CH2:42]N(C)C.Cl.N1[CH2:51][CH2:50]CC1.[C:52](=O)([O-])[O-:53].[K+].[K+].[I-].[K+]>O.CN(C=O)C.C(Cl)Cl>[ClH:1].[F:2][C:3]([F:26])([F:27])[C:4]1[CH:5]=[C:6]([CH:19]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:21]=1)[CH2:7][O:8][CH2:9][CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:11][NH:12][C:52](=[O:53])[C:40]1[CH:41]=[CH:42][C:29]([CH2:28][N:30]2[CH2:33][CH2:34][CH2:32][CH2:31]2)=[CH:51][CH:50]=1

Participants

10

Reactant 6

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866240403-(3,5-Bis(trifluoromethyl)benzyloxy)-2-phenylpropylamine hydrochloride

Product 1

HCID 86624058N-[3-(3,5-bis(trifluoromethyl)benzyloxy)-2-phenylprop yl]-4-pyrrolidin-1-ylmethylbenzamide hydrochlorideYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 70 (2.25 g, 71%) was produced as an oily product from 4-chloromethylbenzoic acid (1.23 g, 7.2 mmol), the compound produced in Example 17 (2.48 g, 6.0 mmol), triethylamine (0.83 mL, 6.0 mmol), WSC.HCl (1.38 g, 7.2 mmol) and CH2Cl2 (20 mL) according to the same manner as Example 30. Compound 70 (1.06 g, 2.0 mmol), pyrrolidine (0.25 mL, 3.0 mmol), potassium carbonate (0.55 g, 4.0 mmol) and potassium iodide (0.1 g) were added to DMF (15 mL) and the mixture was stirred for 20 hours at room temperature. Water was added to the reaction mixture followed by extracting with ethyl acetate. The organic layers were combined, washed with water and a saturated saline solution and dried over anhydrous sodium sulfate. The residual oily product produced by evaporation of the solvent therefrom in vacuo was crystallized from petroleum ether to give Compound 64 (1.12 g, 93%).

Workup

  1. extractionby extracting with ethyl acetate
  2. washwashed with water
  3. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  4. customThe residual oily product produced by evaporation of the solvent
  5. customin vacuo was crystallized from petroleum ether

Sources & evidence

ORD record
ord-090a1ba8e8a142dba751339b572ec39b
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

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