Dichloromethane → 4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methane-sulfonylmethyl)phenyl]piperazine-1-carboxylic acid N-methylamide

HRID 25228Notes

Reaction equation

HRID 25228 reaction equation
ClCCl.[CH3:4][N:5]=[C:6]=[O:7].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[N:16]2[CH2:19][C:18](=[CH:20][S:21]([CH2:24][C:25]3[CH:26]=[C:27]([N:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)[CH:28]=[CH:29][CH:30]=3)(=[O:23])=[O:22])[CH2:17]2)=[CH:11][CH:10]=1>O>[CH3:4][NH:5][C:6]([N:34]1[CH2:35][CH2:36][N:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][S:21]([CH:20]=[C:18]3[CH2:17][N:16]([CH:15]([C:12]4[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=4)[C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)[CH2:19]3)(=[O:22])=[O:23])[CH:26]=2)[CH2:32][CH2:33]1)=[O:7]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12228Methyl IsocyanateHCID 696356951-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine

Product 1

HCID 696356224-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methane-sulfonylmethyl)phenyl]piperazine-1-carboxylic acid N-methylamideYield 110.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 cm3 of dichloromethane and then 11.5 mg of methyl isocyanate 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 4 hours at a temperature close to 20° C., 0.05 cm3 of water is added to the mixture. After stirring for 15 minutes at the same temperature, the reaction medium is dried over magnesium sulfate, filtered on paper and concentrated to dryness under reduced pressure (1 kPa) at a temperature close to 40° C. 66 mg of 4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine-1-carboxylic acid N-methylamide are thus obtained in the form of a beige lacquer [1H NMR spectrum (400 MHz, CDCl3), δ in ppm): 2.75 (s, 3H), 2.85 (d, J=5 Hz, 3H), 3.19 (broad t, J=5.5 Hz, 4H), 3.52 (broad t, J=5.5 Hz, 4H), 3.80 (mt, 2H), 4.33 (mt, 2H), 4.45 (broad q, J=5 Hz, 1H), 4.49 (s, 1H), 6.81 (d, J=8 Hz, 1H), 6.89 (dd, J=8 and 2.5 Hz, 1H), 6.98 (broad s, 1H), from 7.20 to 7.30 (mt, 5H), 7.32 (d, J=8 Hz, 4H)].

Workup

  1. customclose to 20° C.
  2. stirringAfter stirring for 15 minutes at the same temperature
  3. dry with materialthe reaction medium is dried over magnesium sulfate
  4. filtrationfiltered on paper
  5. concentrationconcentrated to dryness under reduced pressure (1 kPa) at a temperature
  6. customclose to 40° C

Sources & evidence

ORD record
ord-1fb274352a7948b1980eb7c6af9f86f2
Source dataset
uspto-grants-2005_02
Patent number
US06858603B2

Reaction notes

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