Hydrochloric Acid → 3-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]benzoic acid;N,N-diethylethanamine

HRID 227460Notes

Reaction equation

HRID 227460 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH:8]([CH2:12][NH:13][C:14](=[O:26])[CH2:15][C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=2)[C:19]([O:21]C)=[O:20])[CH2:7]1.[OH-].[Na+].Cl>O.CO>[CH2:5]([N:6]([CH2:11][CH3:10])[CH2:7][CH3:8])[CH3:4].[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH:8]([CH2:12][NH:13][C:14](=[O:26])[CH2:15][C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=2)[C:19]([OH:21])=[O:20])[CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21963019Methyl 3-[2-({[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}amino)-2-oxoethyl]benzoate

Product 1

HCID 1317259153-[2-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]benzoic acid;N,N-diethylethanamineYield 204.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of Example 56 (0.261 g) in a mixture of water (4 ml) and methanol (12 ml) was added a solution of sodium hydroxide (0.054 g) in water (0.5 ml) and the mixture was stirred at 20° C. for 72 h. The pH of the mixture was adjusted to approximately 6 by the addition of 2N hydrochloric acid and the mixture was purified by solid phase extraction (10 g SCX cartridge), eluting with methanol followed by 10% triethylamine in methanol. Evaporation of the basic fraction in vacuo gave the title compound as a colourless gum, (0.319 g).

Workup

  1. customthe mixture was purified by solid phase extraction (10 g SCX cartridge)
  2. washeluting with methanol
  3. customEvaporation of the basic fraction in vacuo

Sources & evidence

ORD record
ord-733a3baf2fdf43068abec20796d8690c
Source dataset
uspto-grants-2009_07
Patent number
US07560548B2

Reaction notes

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