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Dimethyl Sulfoxide → HCID 68693444, compound

HRID 644124
Notes
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Reaction equation

HRID 644124 reaction equation
CS(C)=O.[F:5][C:6]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:11]=[CH:10][C:7]=1[C:8]#[N:9].Cl[CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[C:31]([F:37])[CH:30]=1.C(N(C(C)C)C(C)C)C>O>[C:33]([C:32]1[CH:35]=[CH:36][C:29]([O:28][CH2:27][CH2:26][CH2:25][N:21]2[CH2:22][CH2:23][CH:18]([CH2:17][CH2:16][CH2:15][O:14][C:12]3[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([F:5])[CH:13]=3)[CH2:19][CH2:20]2)=[CH:30][C:31]=1[F:37])#[N:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 18539959HCID 18539959, compoundHCID 59263044HCID 59263044, compound

Product 1

HCID 68693444HCID 68693444, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
85 °C

Procedure

To a dimethylsulfoxide (4.0 mL) solution of 0.26 g of 2-fluoro-4-[3-(4-piperidinyl)propoxy]benzonitrile and 0.21 g of 4-(3-chloropropoxy)-2-fluorobenzonitrile was added 0.88 mL of N-ethyldiisopropylamine, which was then stirred at 80 to 90° C. for 8 hours and 15 minutes. The reaction mixture was cooled down to room temperature, to which water was then added, followed by extraction with ethyl acetate. The extract was washed twice with water and dried with anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; chloroform:methanol=10:1) to provide 0.25 g of 4-(3-{1-[3-(4-cyano-3-fluorophenoxy)propyl]-4-piperidinyl}propoxy)-2-fluorobenzonitrile as brown solid form.

Workup

  1. additionwas then added
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed twice with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe resultant residue was purified

Sources & evidence

ORD record
ord-48068d53e9ef4d38af20df6eccfe9d45
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700623B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes