Pyridine → 4-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine-1-carboxylic acid methyl ester

HRID 25229Notes

Reaction equation

HRID 25229 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH3:11])=[O:9].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)[N:20]2[CH2:23][C:22](=[CH:24][S:25]([CH2:28][C:29]3[CH:30]=[C:31]([N:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)[CH:32]=[CH:33][CH:34]=3)(=[O:27])=[O:26])[CH2:21]2)=[CH:15][CH:14]=1>C(OCC)(=O)C.O>[CH3:11][O:10][C:8]([N:38]1[CH2:39][CH2:40][N:35]([C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([CH2:28][S:25]([CH:24]=[C:22]3[CH2:21][N:20]([CH:19]([C:16]4[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=4)[C:41]4[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=4)[CH2:23]3)(=[O:26])=[O:27])[CH:30]=2)[CH2:36][CH2:37]1)=[O:9]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 696356951-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine

Product 1

HCID 696355964-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine-1-carboxylic acid methyl esterYield 103.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2 cm3 of pyridine and then 10.4 mg of methyl chloroformate are successively added, at a temperature close to 20° C., to 54.25 mg of 1-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine. After stirring for 6 hours at a temperature close to 20° C., the reaction medium is concentrated to dryness under reduced pressure (5 kPa) at a temperature close to 30° C. The residue obtained is taken up in 5 cm3 of ethyl acetate and 5 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. 62 mg of 4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine-1-carboxylic acid methyl ester are thus obtained in the form of a beige lacquer [1H NMR spectrum (400 MHz, CDCl3), δ in ppm): 2.75 (s, 3H), 3.15 (broad t, J=5.5 Hz, 4H), 3.62 (mt, 4H), 3.74 (s, 3H), 3.80 (mt, 2H), 4.32 (mt, 2H), 4.49 (s, 1H), 6.81 (d, J=8 Hz, 1H), 6.90 (dd, J=8 and 2.5 Hz, 1H), 6.99 (broad s, 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 (5 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-5ba73145204d4e08ba272232a52675ce
Source dataset
uspto-grants-2005_02
Patent number
US06858603B2

Reaction notes

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