Imidazole → 2-Chloro-5-(3-iodopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

HRID 1816065Notes

Reaction equation

HRID 1816065 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24]O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[I:26]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1>ClCCl>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][I:26])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 129886872-Chloro-5-(3-hydroxypropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 689262302-Chloro-5-(3-iodopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamideYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-(3-hydroxypropyl)-N-(tricyclo[3.3.1.1 3,7]dec-1-ylmethyl)-benzamide (5.9 g, Example 6d), iodine (6.2 g, 24.4 mmol), triphenylphosphine (6.4 g, 24.4 mmol) and imidazole (1.66 g, 24.4 mmol) were stirred in dichloromethane (100 ml) at room temperature for 1 h. The reaction was quenched with sat. aq. Na2S2O3 and the layers were separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried (Na2SO4), concentrated and purified by column chromatography on silica (eluting with EtOAc: isohexane/1:3) to afford the subtitled compound as a pale yellow solid (6.8 g)

Workup

  1. customThe reaction was quenched with sat. aq. Na2S2O3
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica (eluting with EtOAc: isohexane/1:3)

Sources & evidence

ORD record
ord-841e3a61a48749648a28f57eea312d7f
Source dataset
uspto-grants-2005_04
Patent number
US06881754B2

Reaction notes

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