Triethylamine → 3-[[2-(1-tert-Butoxycarbonylpiperid-4-yl)ethyl]-amino]-5,6-dichloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one

HRID 965538Notes

Reaction equation

HRID 965538 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.C(N(CC)CC)C.Br[C:25]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[Cl:43])[C:33]2[C:28](=[CH:29][C:30]([Cl:35])=[C:31]([Cl:34])[CH:32]=2)[NH:27][C:26]1=[O:36]>C(Cl)(Cl)Cl.C1COCC1>[C:13]([O:12][C:10]([N:7]1[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][NH:1][C:25]2([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[Cl:43])[C:33]3[C:28](=[CH:29][C:30]([Cl:35])=[C:31]([Cl:34])[CH:32]=3)[NH:27][C:26]2=[O:36])[CH2:9][CH2:8]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylateHCID 219059233-Bromo-5,6-dichloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-one

Product 1

HCID 190764883-[[2-(1-tert-Butoxycarbonylpiperid-4-yl)ethyl]-amino]-5,6-dichloro-3-(2-chlorophenyl)-1,3-dihydroindol-2-oneYield 78.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.05 g of 4-(2-aminoethyl)-1-(tert-butoxycarbonyl)piperidine and 0.46 g of triethylamine in 10 ml of chloroform is added at RT to a solution of 1.8 g of the compound obtained in step C in 50 ml of THF and the mixture is stirred for 2 hours at RT. It is concentrated under vacuum, the residue is taken up with a 5% solution of potassium carbonate and extracted with AcOEt, the organic phase is washed with water and with a saturated solution of NaCl, boiling THF is added to the organic phase, the latter is dried over sodium sulfate and the solvents are partially evaporated off. The crystalline product formed is filtered off to give 1.94 g of the expected product. M.p.=248°-249° C.

Workup

  1. concentrationIt is concentrated under vacuum
  2. extractionextracted with AcOEt
  3. washthe organic phase is washed with water and with a saturated solution of NaCl
  4. additionis added to the organic phase
  5. dry with materialthe latter is dried over sodium sulfate
  6. customthe solvents are partially evaporated off
  7. customThe crystalline product formed
  8. filtrationis filtered off

Sources & evidence

ORD record
ord-4ebc9d8aa0b743bf950d6c5486fa2dff
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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