p-Anisoyl chloride → HCID 15391990, compound

HRID 580928Notes

Reaction equation

HRID 580928 reaction equation
O1CCCC1.[CH3:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1.[CH:17]1([O:22][C:23]2[CH:24]=[C:25]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])[CH2:26][CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH2:21][CH2:20][CH2:19][CH2:18]1.C(N(CC)CC)C>C(OCC)C>[CH:17]1([O:22][C:23]2[CH:24]=[C:25]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])[CH2:26][CH:27]2[CH2:32][CH2:31][N:30]([C:12](=[O:13])[C:11]3[CH:15]=[CH:16][C:8]([O:7][CH3:6])=[CH:9][CH:10]=3)[CH2:29][CH2:28]2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 7477p-Anisoyl chlorideHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 15391991HCID 15391991, compound

Product 1

HCID 15391990HCID 15391990, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 20 ml of tetrahydrofuran (THF) containing 1 g of 4-methoxybenzoyl chloride is added dropwise to a solution of 30 ml of THF containing 0.73 g of 4-(3-cyclopentyloxy-4-methoxybenzyl)piperidine, 0.78 ml of triethylamine and 0.2 g of 4-N,N-dimethylaminopyridine, and the mixture is stirred under argon at room temperature. The reaction mixture is stirred at room temperature for 4 hours, diluted with 150 ml of diethyl ether, washed with a saturated aqueous sodium carbonate solution and then with water, and washed with a 1N HCl solution and then washed again with water. The organic phase is dried over magnesium sulphate and concentrated. The residual oil is filtered over silica by the flash chromatography technique using a toluene/ethanol mixture (97:3) as eluant. 4-(3-Cyclopentyloxy-4-methoxybenzyl)-1-(4-methoxybenzoyl)piperidine is obtained in the form of an oil.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 4 hours
  2. washwashed with a saturated aqueous sodium carbonate solution
  3. washwith water, and washed with a 1N HCl solution
  4. washwashed again with water
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. concentrationconcentrated
  7. filtrationThe residual oil is filtered over silica by the flash chromatography technique

Sources & evidence

ORD record
ord-49fe2bff2d5742379484a913c169677c
Source dataset
uspto-grants-1999_07
Patent number
US05919801

Reaction notes

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