Diethyl Ether → HCID 22557462, compound

HRID 983495Notes

Reaction equation

HRID 983495 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18]([C:23]([NH2:25])=[O:24])=[CH:17]3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][CH2:27][Mg+].[Br-].C(Cl)(=O)[C:31]1[CH:36]=C[C:34]([O:37]C)=[CH:33][CH:32]=1.[Al+3].[Cl-].[Cl-].[Cl-].C[CH2:46][O:47]CC>ClCCl.[Cl-].[Cl-].[Zn+2]>[CH3:46][O:47][C:26]1[CH:27]=[CH:36][CH:31]=[CH:32][C:33]=1[C:34]([C:15]1[C:16]2[C:20](=[CH:21][CH:22]=[C:18]([C:23]([NH2:25])=[O:24])[CH:17]=2)[NH:19][C:14]=1[N:11]1[CH2:10][CH2:9][CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1)=[O:37]

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 7477p-Anisoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 54004669HCID 54004669, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 22557462HCID 22557462, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Acylation at 3-position of the indole ring system was achieved by a procedure of C. X. Yang, et al. (Synth. Commun. 27 (12), 2125 (1997). To a solution of 0.318 g (1.0 mmol) of 5(4-benzylpiperidinyl)-indole carboxamide in dichloromethane was added 2.2 mL (2.2 mmol) of 1 M solution of ZnCl2 in ether followed by the dropwise addition of EtMgBr (1.0 mmol). The mixture was stirred for 1 h and p-anisoyl chloride (180 mg, 1,1 mmol) was added. The suspension was stirred for 1 h and AlCl3 (0.05 mmol) was added. The resultant mixture was stirred for 2 h and was quenched with Sat. NH4Cl solution. The organic layer was washed with aq. NaHCO3 and brine, dried over MgSO4 and filtered. The solvent was evaporated and the product was purified by Silica gel chromatography.

Workup

  1. stirringThe suspension was stirred for 1 h
  2. customwas quenched with Sat. NH4Cl solution
  3. washThe organic layer was washed with aq. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was evaporated
  7. customthe product was purified by Silica gel chromatography

Sources & evidence

ORD record
ord-4d7034d3f6b24349a3318d1181a9bb61
Source dataset
uspto-grants-2005_03
Patent number
US06864260B2

Reaction notes

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