Piperidine → HCID 60155787, compound

HRID 1749831Notes

Reaction equation

HRID 1749831 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]1.[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH:36]=O)=[CH:28]1.N1CCCCC1>CO>[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](/[CH:36]=[C:7]2\[O:8][C:4]3[C:3]([CH2:12][N:13]4[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]4)=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=3[C:6]\2=[O:9])=[CH:28]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10256Indole-3-CarboxaldehydeHCID 60155785HCID 60155785, compound

Product 1

HCID 60155787HCID 60155787, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]-1,4-diazepane-1-carboxylate (0.142 g, 0.392 mmol) in methanol (2 mL) was added with 1H-indole-3-carboxaldehyde (0.0569 g, 0.392 mmol) and piperidine (0.00334 g, 0.0392 mmol), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated, and the resulting residue was subjected to silica gel column chromatography (chloroform/methanol). The resulting solid crude product was washed with a mixed solvent of hexane and ethyl acetate to obtain tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)-1,4-diazepane-1-carboxylate (0.141 g, 73%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washThe resulting solid crude product was washed with a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-3a03bdfbfc8442b4869511230f2b109d
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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