Triethylamine → 2-((1-Benzyl-4-(4-cyclopropylpiperazin-1-yl)-piperidin-4-yl)methyl)isoindolin-1-one

HRID 45999

Reaction equation

HRID 45999 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:23][NH2:24])([N:14]2[CH2:19][CH2:18][N:17]([CH:20]3[CH2:22][CH2:21]3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:26][C:27]1[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=1[C:29](OC)=[O:30].C(N(CC)CC)C>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:23][N:24]2[CH2:26][C:27]3[C:28](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:29]2=[O:30])([N:14]2[CH2:19][CH2:18][N:17]([CH:20]3[CH2:22][CH2:21]3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 57989589(1-Benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidin-4-yl)methanamine

Product 1

HCID 579895902-((1-Benzyl-4-(4-cyclopropylpiperazin-1-yl)-piperidin-4-yl)methyl)isoindolin-1-oneYield 51%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (1-benzyl-4-(4-cyclopropylpiperazin-1-yl)piperidin-4-yl)methanamine (see above: synthesis of amine AM12) (1.22 mmol, 1.0 equiv.) and methyl 2-(bromomethyl)benzoate (1.22 mmol, 1.0 equiv.) in benzene (3 ml/mmol) was added triethylamine (2.44 mmol, 2.0 equiv.) and the resulting reaction mixture was refluxed for 25 h. The mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and the organic layer was successively washed with water and brine. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to give the crude product which was purified by silica gel column chromatography. Yield: 51%.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 25 h
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic layer was successively washed with water and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-feca17fae52f41da8e02615f3d8018a8
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Linked notes

Loading…