Potassium Carbonate → HCID 70246964, compound

HRID 325060Notes

Reaction equation

HRID 325060 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:35]([C:37]1[CH:45]=[CH:44][C:40]([C:41](Cl)=[O:42])=[CH:39][CH:38]=1)#[N:36]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][NH:27][C:41](=[O:42])[C:40]3[CH:44]=[CH:45][C:37]([C:35]#[N:36])=[CH:38][CH:39]=3)=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 801724-Cyanobenzoyl chlorideHCID 20649558HCID 20649558, compound

Product 1

HCID 70246964HCID 70246964, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of {4-[3-(4-aminomethyl-phenoxy)-propoxy]-benzyl}-carbamic acid tert-butyl ester prepared in Example 78 (3.00 g,7.76 mmol) in THF (30 mL) was added a 10% aqueous solution of potassium carbonate (53.90 mL, 38.81 mmol). 4-Cyanobenzoyl chloride (1.29 g, 7.76 mmol) was then added in one portion and the reaction mixture was stirred at room temperature for 16 hours. The mixture was then diluted with EtOAc (150 mL), washed with 1N aqueous HCl (2×150 mL), dried over MgSO4, and concentrated to provide the desired compound as a yellow solid (2.41 g, 60% yield) which did not require any further purification.

Workup

  1. washwashed with 1N aqueous HCl (2×150 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f2b21bb4ccf44f38b33c8de7b9f05541
Source dataset
uspto-grants-2001_04
Patent number
US06221914B1

Reaction notes

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