Piperidine → HCID 86681964, compound

HRID 1749772Notes

Reaction equation

HRID 1749772 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[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.[S:26]([N:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]([CH:45]=O)=[CH:37]1)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27].N1CCCCC1>CO>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])/[C:7](=[CH:45]/[C:38]3[C:39]4[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=4)[N:36]([S:26]([C:29]4[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=4)(=[O:28])=[O:27])[CH:37]=3)/[O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 7358171-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehydeHCID 60155786Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate

Product 1

HCID 86681964HCID 86681964, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.697 g, 2.00 mmol) obtained in Example A16, Step 1 in methanol (10 mL) was added with 1-tosyl-1H-indole-3-carboxaldehyde (0.599 g, 2.00 mmol) synthesized in Step 1 and piperidine (0.0170 g, 0.200 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was added with methanol (2 mL), and the solid was suspended in methanol and thereby washed to obtain tert-butyl (Z)-4-({6-hydroxy-3-oxo-2-[(1-tosyl-1H-indol-3-yl)methylene]-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.470 g, 37%).

Workup

  1. washwashed

Sources & evidence

ORD record
ord-f03107c62aa94fc3a9cfa9dbfb0fb55e
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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