Piperidine → HCID 54352759, compound

HRID 2120239

Reaction equation

HRID 2120239 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1.N1CCCCC1>C(O)C>[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[CH:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[C:17]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[CH:18]=1)[C:7](=[O:13])[NH:8]2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 109430044-(2-Hydroxyethyl)indolin-2-oneHCID 219810244-Methoxy-3-(thiophen-2-yl)benzaldehyde

Product 1

HCID 54352759HCID 54352759, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.6 g, 9.2 mmol), 4-methoxy-3-thiophen-2-yl-benzaldehyde (2 g, 9.2 mmol) and piperidine (4.5 mL, 85 mmol) in ethanol (46 mL) was heated to reflux for overnight. The reaction mixture was concentrated and the residue was chromatographed on a column of silica gel to give 1.63 g (47%) of 4-(2-hydroxy-ethyl)-3-(4-methoxy-3-thiophen-2-yl-benzylidene)-1,3-dihydro-indol-2-one as a yellow orange solid. 1HNMR (300 MHz, DMSO-d6) δ 10.53 (s, br, 1H, NH), 8.73 (d, J=2.1 Hz, 1H), 8.10 (dd, J=2.2 & 9.1 Hz, 1H), 7.74 (s, 1H, H-vinyl), 7.56-7.65 (m, 2H), 7.07-7.22 (m, 3H), 6.81 (d, J=7.5 Hz, 1H), 6.68 (dd, J=0.6, 7.5 Hz, 1H), 4.87 (t, J=4.5 Hz, 1H, OH), 3.97 (s, 3H, OCH3), 3.68-3.75 (m, 2H, CH2CH2OH), 3.09 (t, J=4.5 Hz, 2H, CH2CH2OH).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-026f27878bb8434eb2bd152067b6cb4c
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Linked notes

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