Sodium Hydroxide → 4-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide

HRID 376062Notes

Reaction equation

HRID 376062 reaction equation
Cl.[NH2:2][N:3]=[CH:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:30]=[CH:29][C:19]([C:20]([N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:18][C:17]=2[O:31][CH3:32])=[CH:7][CH:6]=1.[OH-].[Na+]>O>[NH2:2][N:3]=[CH:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:30]=[CH:29][C:19]([C:20]([N:22]([CH:26]([CH3:27])[CH3:28])[CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:18][C:17]=2[O:31][CH3:32])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 677447554-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide monohydrochloride

Product 1

HCID 1838004-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamideYield 99.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred, 0° C. solution of 4-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide monohydrochloride (1.9 g, 3.86 mmol) in 20 mL water is treated with 20 mL of 1.0N aqueous sodium hydroxide. The solution is extracted sequentially with four 50 mL portions of dichloromethane. The combined organic solution is washed with brine, dried over sodium sulfate and concentrated to give 4-[5-[4-(aminoiminomethyl)phenoxy] pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide (1.75 g) as a colorless foam. A portion of this material (500 mg, 1.1 mmol) is dissolved in 1 mL ethanol and treated dropwise with a solution of maleic acid (127 mg) in 1 mL ethanol. Diethyl ether (10 mL) is added slowly dropwise to induce crystallization. The crystalline product is collected by filtration, washed with ether and dried to give 4-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide (Z)-2-butenedioate (1:1), mp=145°-146° C.

Workup

  1. extractionThe solution is extracted sequentially with four 50 mL portions of dichloromethane
  2. washThe combined organic solution is washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-925ec2204112417485da0eb3fa5e5199
Source dataset
uspto-grants-1996_01
Patent number
US05488160

Reaction notes

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