Methanol → HCID 19002835, compound

HRID 2259212Notes

Reaction equation

HRID 2259212 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=O)=[CH:15][CH:14]=3)=[O:12])=[C:9]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[S:8][C:7]=2[CH:35]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.CO>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH:11]([C:13]3[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:17][CH:18]=3)[OH:12])=[C:9]([CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[S:8][C:7]=2[CH:35]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 19002783HCID 19002783, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19002835HCID 19002835, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

353 mg of (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-piperidinylcarbonyl)ethyl]phenyl]methanone was dissolved in 30 ml of THF, 850 mg of lithium aluminum hydride was added, and the mixture was refluxed with heating for 1 hour. A small quantity of water was added to the reaction mixture, followed by stirring, 1 ml of methanol was added, followed by stirring for 5 minutes, and 5 ml of ethyl acetate was added, followed by stirring for 5 minutes. The mixture was filtered using a super cell, the filtrate was concentrated under reduced pressure, and the resultant crude product was purified by TLC (developing solvent, chloroform:methanol=19:1) to obtain 107 mg of (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[3-(1-piperidinyl)propyl]phenyl]methanol.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 1 hour
  3. stirringby stirring for 5 minutes
  4. stirringby stirring for 5 minutes
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe resultant crude product was purified by TLC (developing solvent, chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-718cd4acb0d44c87b2dc1e80f7c74b75
Source dataset
uspto-grants-1995_12
Patent number
US05472962

Reaction notes

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