1,1'-Carbonyldiimidazole → 2-Chloro-3-fluoro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 380684Notes

Reaction equation

HRID 380684 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:24]12([CH2:34][NH2:35])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>CN(C)C=O>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:35][CH2:34][C:24]12[CH2:33][CH:28]3[CH2:27][CH:26]([CH2:32][CH:30]([CH2:29]3)[CH2:31]1)[CH2:25]2)=[O:6]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 3026202-Chloro-3-fluorobenzoic acid

Product 1

HCID 206700332-Chloro-3-fluoro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-3-fluorobenzoic acid (0.098 g) and carbonyldiimidazole (0.091 g), in N,N-dimethylformamide (3.0 ml) was stirred for 2.5 hours at room temperature. 1-Adamantanemethylamine (0.1 ml) was then added and stirring continued overnight. The reaction mixture was partitioned between ethyl acetate and 2N hydrochloric acid and the organic layer was separated, washed with 10% aqueous sodium hydroxide, water and brine and then dried over sodium sulphate (Na2SO4). The organic layer was subsequently concentrated under reduced pressure to yield the tire compound as a white solid (0.138 g).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 2N hydrochloric acid
  2. customthe organic layer was separated
  3. washwashed with 10% aqueous sodium hydroxide, water and brine
  4. dry with materialdried over sodium sulphate (Na2SO4)
  5. concentrationThe organic layer was subsequently concentrated under reduced pressure

Sources & evidence

ORD record
ord-701166d3079747ceb0ca4b2eeea472db
Source dataset
uspto-grants-2001_10
Patent number
US06303659B2

Reaction notes

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