Dimethyl Sulfoxide → HCID 68693444, compound

HRID 644124Notes

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]

Participants

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

additionwas then added
extractionfollowed by extraction with ethyl acetate
washThe extract was washed twice with water
dry with materialdried with anhydrous magnesium sulfate
distillationby distilling off the solvent under reduced pressure
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

Loading…