HCID 19002835, compound → HCID 19002775, compound

HRID 2259216Notes

Reaction equation

HRID 2259216 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:15][CH:14]=3)[OH:12])=[C:9]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[S:8][C:7]=2[CH:34]=1>[O-2].[O-2].[O-2].[Cr+6].N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:17][CH:18]=3)=[O:12])=[C:9]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[S:8][C:7]=2[CH:34]=1

Participants

4

Reactant 1

HCID 19002835HCID 19002835, compound

Product 1

HCID 19002775HCID 19002775, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1049PyridineSolvent2×

Procedure

88 mg of chromium trioxide was added to 5 ml of pyridine to give a yellow gruel-like solution, a pyridine solution of 105 mg of (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[3-(1-piperidinyl)propyl]phenyl]methanol was added, and the mixture was stirred at room temperature for 1 hour. After addition of ice to the reaction mixture, the mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resultant crude product was purified by TLC (developing solvent, chloroform:methanol=19:1) to obtain 47 mg of (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[3-(1-piperidinyl)propyl]phenyl]methanone.

Workup

  1. customto give a yellow gruel-like solution
  2. additionAfter addition of ice to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe resultant crude product was purified by TLC (developing solvent, chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-4e9e339304574461a0757dd3f8e4de6a
Source dataset
uspto-grants-1995_12
Patent number
US05472962

Reaction notes

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