Chlorine → HCID 23294565, compound

HRID 1955201Notes

Reaction equation

HRID 1955201 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][C:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:10][CH:9]=2)=[CH:5][CH:4]=1.[Cl:26]Cl.CO.C(Cl)(Cl)Cl>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[ClH:2].[Cl:1][CH:9]1[C:8]([Cl:26])([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:25][CH:24]=2)[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[CH2:10]1

Participants

6

Reactant 3

HCID 24526Chlorine2×HCID 21584188Chloroform methanolHCID 23294227HCID 23294227, compound

Product 1

HCID 23294565HCID 23294565, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 4-(4-chlorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)-1,2,5,6-tetrahydropyridine hydrochloride (70 mg, 136 μmol) in CHCl3 (10 mL) a dilute solution of Cl2 in CCl4 was added in portions. After each addition the reaction was checked by TLC (1% MeOH/CHCl3). Cl2 addition was continued until all the starting material was converted to the much higher Rf product spot. The reaction mixture was washed with dilute NH4OH and the organic portion was filtered (cotton). Solvent removal gave a yellow oil. The oil was purified on silica gel with CHCl3 elution to give the free base of the title compound as a pale yellow oil (37 mg, 49%). The free base was converted to hydrochloride as a pale beige powder (40 mg): mp 78-83° C. (foams), 1H NMR (CDCl3) 1.98 (d, J=15 Hz, 1H), 2.95-4.00 (m, 9H), 4.10-4.20 (m, 1H), 4.38-4.75 (m, 2H), 6.79-7.02 (m, 2H), 7.27-7.37 (m, 2H), 12.48 (bs, 1H); HRMS calcd for C20H21Cl3FNO 415.0673, found 415.0664.

Workup

  1. additionAfter each addition the reaction
  2. washThe reaction mixture was washed with dilute NH4OH
  3. filtrationthe organic portion was filtered (cotton)
  4. customSolvent removal
  5. customgave a yellow oil
  6. customThe oil was purified on silica gel with CHCl3 elution

Sources & evidence

ORD record
ord-c9e27eac19044cb29da235bce82119ff
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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