Methyl iodide → HCID 23044936, compound

HRID 2107943Notes

Reaction equation

HRID 2107943 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10](=[O:24])[C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([NH2:18])=[CH:13][C:12]=1[O:19][CH2:20][CH:21]1[CH2:23][CH2:22]1)[CH2:2]2.[I:25][CH3:26]>CC(C)=O>[CH3:26][I:25].[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10](=[O:24])[C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([NH2:18])=[CH:13][C:12]=1[O:19][CH2:20][CH:21]1[CH2:22][CH2:23]1)[CH2:2]2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 713424-Amino-N-(1-azabicyclo[2.2.2]octan-3-yl)-5-chloro-2-(cyclopropylmethoxy)benzene-1-carboximidic acid

Product 1

HCID 23044936HCID 23044936, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-(1-azabicyclo[2.2.2]oct-3-yl)-2-cyclopropylmethoxy-4-amino-5-chlorobenzamide (3.5 g; 0.01 mol) in acetone (200 ml), iodomethane (2.8 g; 0.02 moles) was added and the resulting mixture stirred to room temperature for 20 hours. The precipitated solid was collected, washed with acetone and dried to give N-(1-azabicyclo[2.2.2]oct-3-yl)-2-cyclopropylmethoxy-4-amino-5-chlorobenzamide methyl iodide (3.9 g), m.p. 274°-276° C. (d) (after recrystallisation from a mixture of acetonitrile and water).

Workup

  1. customThe precipitated solid was collected
  2. washwashed with acetone
  3. customdried

Sources & evidence

ORD record
ord-225c71a2b6494669a2eb42d333d38f53
Source dataset
uspto-grants-1990_06
Patent number
US04937236

Reaction notes

Loading…