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Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl ester → (4-Isopropyl-piperazin-1-yl)-[1-(1-methyl-piperidin-3-ylmethyl)-1H-indol-5-yl]-methanone

HRID 2113470
Notes
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Reaction equation

HRID 2113470 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]3)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC([O-])(C)C.[K+].[CH3:27][N:28]1[CH2:33][CH2:32][CH2:31][CH:30]([CH2:34]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:29]1>C1COCC1>[CH:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[N:1]([CH2:34][CH:30]2[CH2:31][CH2:32][CH2:33][N:28]([CH3:27])[CH2:29]2)[CH:2]=[CH:3]3)=[O:11])[CH2:17][CH2:16]1)([CH3:20])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 21184160Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl ester2×HCID 23665647Potassium tert-butoxideHCID 57752818Methanone,1h-indol-5-yl[4-(1-methylethyl)-1-piperazinyl]-2×

Product 1

HCID 23652334(4-Isopropyl-piperazin-1-yl)-[1-(1-methyl-piperidin-3-ylmethyl)-1H-indol-5-yl]-methanoneYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture of 1.06 g (3.9 mmol) (1H-indol-5-yl)-(4-isopropyl-piperazin-1-yl)-methanone (intermediate 1); 0.484 g (4.3 mmol) KOtBu and 1.33 g (4.7 mmol) toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl ester (intermediate 6) in 20 mL THF was shaken at 60° C. for 3 h. After evaporation of all volatiles a mixture ethyl acetate was added and washed with water. The organic phase was dried with MgSO4 and evaporated to dryness. The residue was purified by column chromatography on silica eluting with a solvent mixture formed from DCM, methanol NEt3. The combined product fractions were evaporated to yield 1.44 g (91%) of the title compound as light yellow gum. MS(m/e): 383.5 (MH+).

Workup

  1. customAfter evaporation of all volatiles a mixture ethyl acetate
  2. additionwas added
  3. washwashed with water
  4. dry with materialThe organic phase was dried with MgSO4
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica eluting with a solvent mixture
  7. customformed from DCM, methanol NEt3
  8. customThe combined product fractions were evaporated

Sources & evidence

ORD record
ord-49b392f28f494bed8baf1f129c963479
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07432255B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes