Piperidine → HCID 86681968, compound

HRID 1749775Notes

Reaction equation

HRID 1749775 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.[F:26][C:27]([F:49])([F:48])[C:28]1[CH:33]=[CH:32][C:31]([S:34]([N:37]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]([CH:46]=O)=[CH:38]2)(=[O:36])=[O:35])=[CH:30][CH:29]=1.N1CCCCC1>CO>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])/[C:7](=[CH:46]/[C:39]3[C:40]4[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=4)[N:37]([S:34]([C:31]4[CH:32]=[CH:33][C:28]([C:27]([F:49])([F:26])[F:48])=[CH:29][CH:30]=4)(=[O:36])=[O:35])[CH:38]=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 60155786Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylateHCID 86681967HCID 86681967, compound

Product 1

HCID 86681968HCID 86681968, compoundYield 77.1%

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 (0.0500 g, 0.144 mmol) obtained in Example A16, Step 1 in methanol (0.6 mL) was added with 1-[4-(trifluoromethyl)phenylsulfonyl]-1H-indole-3-carboxaldehyde (0.0509 g, 0.144 mmol) and piperidine (0.00123 g, 0.0144 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was added with methanol (1 mL), and the solid was suspended in methanol and thereby washed to obtain tert-butyl (Z)-4-([6-hydroxy-3-oxo-2-({1-[4-(trifluoromethyl)phenylsulfonyl]-1H-indol-3-yl}methylene)-2,3-dihydrobenzofuran-7-yl]methyl)piperazine-1-carboxylate (0.0759 g, 77%).

Workup

  1. washwashed

Sources & evidence

ORD record
ord-53358bbde2d04ca58da243cd38c8083f
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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