Triethylamine → HCID 19076562, compound

HRID 234489Notes

Reaction equation

HRID 234489 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]([CH3:35])=[C:31]([Cl:34])[CH:32]=2)[NH:27][C:26]1=[O:36]>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]([CH3:35])=[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

5

Reactant 3

HCID 8471TriethylamineHCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylateHCID 19076402HCID 19076402, compound

Product 1

HCID 19076562HCID 19076562, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.35 g of 4-(2-aminoethyl)-1-(tert-butoxycarbonyl)piperidine and 1.75 g of triethylamine in 20 ml of THF is added dropwise at RT to a solution of 2.1 g of 3-bromo-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-6-methylindol-2-one, obtained in step B' of Preparation 71, in 20 ml of THF and the reaction mixture is stirred for 1 hour at RT. It is concentrated under vacuum, the residue is taken up with 400 ml of AcOEt and 50 ml of THF, the resulting suspension is washed twice with a 5% solution of sodium carbonate, with water and with a saturated solution of NaCl and, after decantation, the solid in suspension is filtered off. The solid is dissolved in 400 ml of boiling THF and dried over sodium sulfate and the solvent is partially evaporated off under vacuum. The crystalline product formed is filtered off to give 1.65 g of the expected product. M.p.=245°-248° C.

Workup

  1. customobtained in step B'
  2. customof Preparation 71
  3. concentrationIt is concentrated under vacuum
  4. washthe resulting suspension is washed twice with a 5% solution of sodium carbonate, with water and with a saturated solution of NaCl
  5. filtrationafter decantation, the solid in suspension is filtered off
  6. dissolutionThe solid is dissolved in 400 ml of boiling THF
  7. dry with materialdried over sodium sulfate
  8. customthe solvent is partially evaporated off under vacuum
  9. customThe crystalline product formed
  10. filtrationis filtered off

Sources & evidence

ORD record
ord-c8c1de0125bf4fce9b0bb74da8e1a3a9
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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