Triethylamine → HCID 68435542, compound

HRID 277135Notes

Reaction equation

HRID 277135 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[N:16]2[CH2:19][CH:18]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH2:17]2)=[CH:11][CH:10]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>ClCCl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)[N:16]2[CH2:19][CH:18]([N:20]([CH2:21][C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)[S:36]([CH3:35])(=[O:38])=[O:37])[CH2:17]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22628971HCID 22628971, compound

Product 1

HCID 68435542HCID 68435542, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

346 mm3 of triethylamine are added, at room temperature under an argon atmosphere, to a solution of 398 mg of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(pyrid-4-ylmethyl)amine in 8 cm3 of dichloromethane. The mixture is cooled to around 0° C. before adding thereto 155 mm3 of methylsulfonyl choride, and then it is stirred at room temperature for 3 hours. The reaction mixture is diluted with 35 cm3 of dichloromethane and is then washed with twice 20 cm3 of distilled water. The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by flash chromatography on silica gel [eluent:dichloromethane/methanol (97/3 by volume)]. 288 mg of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(pyrid-4-ylmethyl)methylsulfonamide are obtained in the form of a cream-colored foam [1H NMR spectrum (300 MHz, CDCl3, δ in ppm):2.83 (s:3H); 3.02 (broad t, J=7.5 Hz: 2H); 3.40 (broad t, J=7.5 Hz: 2H); 4.23 (s: 1H); 4.43 (mt: 1H); 4.57 (s: 2H); from 7.20 to 7.35 (mt: 8H); 7.32 (broad d, J=5.5 Hz: 2H); 8.60 (broad d, J=5.5 Hz: 2H)].

Workup

  1. additionbefore adding
  2. washis then washed with twice 20 cm3 of distilled water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue obtained
  7. customis purified by flash chromatography on silica gel [eluent:dichloromethane/methanol (97/3 by volume)]

Sources & evidence

ORD record
ord-b64ceba98fb44e9d843c17b696032695
Source dataset
uspto-grants-2002_03
Patent number
US06355631B1

Reaction notes

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