Triethylamine → HCID 14835772, compound

HRID 1709262Notes

Reaction equation

HRID 1709262 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8](/[CH:11]=[CH:12]/[C:13]([OH:15])=O)[CH:9]=2)[CH:4]=[CH:3]1.C(N(CC)CC)C.C(Cl)(=O)OCC.O.O.[N:31]1([CH:37]2[C:47]3[C:42](=[N:43][CH:44]=[CH:45][CH:46]=3)[CH2:41][CH2:40][C:39]3[CH:48]=[CH:49][CH:50]=[CH:51][C:38]2=3)[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>C(Cl)Cl.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8](/[CH:11]=[CH:12]/[C:13]([N:34]3[CH2:35][CH2:36][N:31]([CH:37]4[C:47]5[C:42](=[N:43][CH:44]=[CH:45][CH:46]=5)[CH2:41][CH2:40][C:39]5[CH:48]=[CH:49][CH:50]=[CH:51][C:38]4=5)[CH2:32][CH2:33]3)=[O:15])[CH:9]=2)[CH:4]=[CH:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14835757HCID 14835757, compoundHCID 23037272HCID 23037272, compound

Product 1

HCID 14835772HCID 14835772, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.01 g of (E)-3-(1-methyl-6-indolyl)acrylic acid was suspended in 20 ml of methylene chloride. 560 mg of triethylamine was added thereto. To the mixture was dropwise added 570 mg of ethyl chlorocarbonate at -30° to -20° C. The mixture was stirred for 1 hour at the same temperature. To the reaction mixture was added 1.73 g of 5-(piperazin-1-yl)-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridine dihydrate. The mixture was stirred for 1 hour at room temperature. To the reaction mixture was added 20 ml of water. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: n-hexane/acetone=5/1) to obtain 1.73 g of 5-[4-{(E)-3-(1-methyl-6-indolyl)acryloyl}piperazin-1-yl]-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridine.

Workup

  1. customat -30° to -20° C
  2. stirringThe mixture was stirred for 1 hour at room temperature
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by a column chromatography (eluant: n-hexane/acetone=5/1)

Sources & evidence

ORD record
ord-cd84ea51172c4cd09a218ef55a6e646e
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

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