Dimethylformamide → N,N-diethylethanamine;methyl butanoate

HRID 323234

Reaction equation

HRID 323234 reaction equation
[CH3:1][O:2][C:3]1C=[C:5]([CH:39]=[C:40](OC)[C:41]=1OC)[C:6]([N:8]1[CH2:12][CH2:11][C:10](CCN2CCC(NC3NC4C=CC=CC=4N=3)CC2)(C2C=CC(Cl)=C(Cl)C=2)[CH2:9]1)=O.CN(C)C=[O:49].[H-].[Na+].C(OCCCl)C>ClCCl.CO.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:40]([CH2:41][C:3]([O:2][CH3:1])=[O:49])[CH3:39].[CH2:6]([N:8]([CH2:12][CH3:11])[CH2:9][CH3:10])[CH3:5]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 24758Sodium hydrideHCID 98743601-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine

Product 1

HCID 131722484N,N-diethylethanamine;methyl butanoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21980445Ethyl acetate methanol triethylamineSolvent

Conditions

Temperature
100 °C

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine (0.54 g, 0.82 mmol) and dimethylformamide (15 mL). Add sodium hydride (0.07 g, 60% in oil, 1.8 mmol). After 1 hour, add 2-chloroethyl ethyl ether (1 mL). Heat to 100° C. After 18 hours, cool to ambient temperature and dilute the reaction mixture with dichloromethane. Extract three times with water, dry the organic layer over Na2SO4, filter and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 25/75/1 methanol/ethyl acetate/triethylamine. Collect the product containing fractions, evaporate in vacuo to give a residue, and chromatograph on silica gel eluting with 20/80/0.5 methanol ethyl acetate/triethylamine to give the title compound: Rf=0.23 (silica gel, 30% methanol/ethyl acetate).

Workup

  1. waitAfter 18 hours
  2. temperaturecool to ambient temperature
  3. extractionExtract three times with water
  4. dry with materialdry the organic layer over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue
  8. customCollect the product
  9. additioncontaining fractions
  10. customevaporate in vacuo

Sources & evidence

ORD record
ord-ba28978f1ed94c70867ed611c4592984
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Linked notes

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