Piperidine → HCID 131733601, compound

HRID 1749848Notes

Reaction equation

HRID 1749848 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]2[C:13](=[O:16])[CH2:14][O:15][C:11]=2[C:10]=1[CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]([CH:42]=O)=[CH:34]1.N1CCCCC1>CO>[NH:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](/[CH:42]=[C:14]2\[O:15][C:11]3[C:10]([CH2:19][N:20]4[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]4)=[C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:18]=[CH:17][C:12]=3[C:13]\2=[O:16])=[CH:34]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10256Indole-3-CarboxaldehydeHCID 71278568HCID 71278568, compound

Product 1

HCID 131733601HCID 131733601, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of tert-butyl 4-{[6-(benzyloxy)-3-oxo-2,3-dihydrobenzofuran-7-yl]methyl}piperazine-1-carboxylate (0.198 g, 0.452 mmol) in methanol (1.8 mL) was added with indole-3-carboxaldehyde (0.0656 g, 0.452 mmol) and piperidine (0.0308 g, 0.362 mmol), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, and then the precipitated yellow solid was collected by filtration to obtain tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-6-(benzyloxy)-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.141 g, 55%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe precipitated yellow solid was collected by filtration

Sources & evidence

ORD record
ord-b175612699714f51bb4a08659a136fad
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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