Pyridine → 4-Acetyl 1-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine

HRID 25231Notes

Reaction equation

HRID 25231 reaction equation
N1C=CC=CC=1.C(O[C:11](=[O:13])[CH3:12])(=O)C.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=2)[N:22]2[CH2:25][C:24](=[CH:26][S:27]([CH2:30][C:31]3[CH:32]=[C:33]([N:37]4[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]4)[CH:34]=[CH:35][CH:36]=3)(=[O:29])=[O:28])[CH2:23]2)=[CH:17][CH:16]=1>C(OCC)(=O)C.O>[C:11]([N:40]1[CH2:41][CH2:42][N:37]([C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([CH2:30][S:27]([CH:26]=[C:24]3[CH2:23][N:22]([CH:21]([C:18]4[CH:17]=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=4)[C:43]4[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=4)[CH2:25]3)(=[O:28])=[O:29])[CH:32]=2)[CH2:38][CH2:39]1)(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 696356951-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine

Product 1

HCID 696357084-Acetyl 1-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazineYield 89.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2 cm3 of pyridine and then 11.5 mg of acetic anhydride are successively added, at a temperature close to 20° C., to 54 mg of 1-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine. After stirring for 23 hours at a temperature close to 20° C., the reaction medium is concentrated to dryness under reduced pressure (1 kPa) at a temperature close to 30° C. The residue obtained is taken up in 5 cm3 of ethyl acetate and 2 cm3 of water. After separating after settling out, the organic phase is washed with 2 cm3 of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (1 kPa) at a temperature close to 40° C. 52 mg of 4-acetyl 1-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine are thus obtained in the form of a beige foam [1H NMR spectrum (300 MHz, CDCl3), δ in ppm): 2.16 (s, 3H), 2.77 (s, 3H), from 3.10 to 3.25 (mt, 4H), 3.63 (broad t, J=5.5 Hz, 2H), 3.78 (broad t, J=5.5 Hz, 2H), 3.82 (mt, 2H), 4.34 (mt, 2H), 4.50 (s, 1H), 6.84 (broad d, J=8 Hz, 1H), 6.92 (dd, J=8 and 2 Hz, 1H), 7.02 (mt, 1H), from 7.20 to 7.40 (mt, 9H)].

Workup

  1. customclose to 20° C.
  2. concentrationthe reaction medium is concentrated to dryness under reduced pressure (1 kPa) at a temperature
  3. customclose to 30° C
  4. customThe residue obtained
  5. customAfter separating
  6. washthe organic phase is washed with 2 cm3 of water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (1 kPa) at a temperature
  10. customclose to 40° C

Sources & evidence

ORD record
ord-5c44ca73151846698fd160449716fb55
Source dataset
uspto-grants-2005_02
Patent number
US06858603B2

Reaction notes

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