Piperidine → HCID 86681971, compound

HRID 1749778Notes

Reaction equation

HRID 1749778 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.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([N:36]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]([CH:45]=O)=[CH:37]2)(=[O:35])=[O:34])=[CH:29][CH:28]=1.N1CCCCC1>CO>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([S:33]([N:36]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38](/[CH:45]=[C:7]3\[O:8][C:4]4[C:3]([CH2:12][N:13]5[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]5)=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=4[C:6]\3=[O:9])=[CH:37]2)(=[O:34])=[O:35])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 60155786Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylateHCID 85866393HCID 85866393, compound

Product 1

HCID 86681971HCID 86681971, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

tert-Butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.100 g, 0.287 mmol) obtained in Example A16, Step 1 and 1-(4-chlorophenylsulfonyl)-1H-indole-3-carboxaldehyde (0.0918 g, 0.287 mmol) were stirred overnight at room temperature in methanol (1.2 mL) in the presence of piperidine (0.00244 g, 0.0287 mmol). The reaction mixture was further added with methanol (1 mL), and the solid was suspended in methanol and thereby washed to obtain tert-butyl (Z)-4-[(2-{[1-(4-chlorophenylsulfonyl)-1H-indol-3-yl]methylene}-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.161 g, 86%).

Workup

  1. washwashed

Sources & evidence

ORD record
ord-1d31afc68e9a437e8eef4689fb0d7b84
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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