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Sodium Chloride → HCID 18753182, compound

HRID 1838114
Notes
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Reaction equation

HRID 1838114 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9]/[C:8](=[CH:11]/[C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)/[CH:7]=[C:6]1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH3:3].C1CCC(N=C=NC2CCCCC2)CC1.O[CH:45]1[CH2:50][C:49](=O)[NH:48][C:46]1=O.C(NCC)C.[Cl-].[Na+]>CN(C)C=O>[CH3:3][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9]/[C:8](=[CH:11]/[C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([N:48]([CH2:49][CH3:50])[CH2:46][CH3:45])=[O:17])/[CH:7]=[C:6]1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH3:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8021DiethylamineHCID 10868DicyclohexylcarbodiimideHCID 15541115HCID 15541115, compoundHCID 181836963-Hydroxypyrrolidine-2,5-dione

Product 1

HCID 18753182HCID 18753182, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1.8 g of the Z-3-[4-dimethylaminomethyl-3-(3-methoxy-phenyl)-cyclohex-2-enylidenemethyl]-benzoic acid base prepared according to example 4 were dissolved in 50 ml analytical grade dimethylformamide, and 2 g DCC and 1.1 g hydroxysuccinimide were added at 0° C. to 15° C. The mixture was stirred at 0° C. for one hour and 2 ml diethylamine were then added dropwise at this temperature. The mixture was stirred at 0° C. for an additional hour and then at room temperature for four days. The reaction mixture was poured on to 300 ml saturated sodium chloride solution and the mixture was then extracted 3 times with 250 ml ethyl acetate each time. The organic phases were washed with 50 ml saturated sodium chloride solution and then dried over magnesium sulfate. The solvent was removed in vacuo. The residue was chromatographed on silica gel with ethyl acetate/methanol=6/5. 0.87 g Z-3-[4-dimethylaminomethyl-3-(3-methoxy-phenyl)-cyclohex-2-enylidenemethyl]-N,N-diethyl-benzamide base was obtained in this way in the form of an orange-yellow oil. To liberate the hydrochloride, the oil was dissolved in 5 ml acetone, and an equimolar amount of trimethylchlorosilane and water was added. 0.52 g (22.1% of theory) of the title compound 34 was obtained in this way in the form of white crystals.

Workup

  1. additionwere added at 0° C. to 15° C
  2. stirringThe mixture was stirred at 0° C. for an additional hour
  3. waitat room temperature for four days
  4. extractionthe mixture was then extracted 3 times with 250 ml ethyl acetate each time
  5. washThe organic phases were washed with 50 ml saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. customThe residue was chromatographed on silica gel with ethyl acetate/methanol=6/5

Sources & evidence

ORD record
ord-1b183fac29834650bc5e4f50b8855a72
Source dataset
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06673794B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes