Ethanethiol → 11-{4-[2-(Piperidin-1-yl)ethoxy]phenyl}-11H-benzo[a]fluorene-3,9-diol

HRID 1885918Notes

Reaction equation

HRID 1885918 reaction equation
C[O:2][C:3]1[CH:36]=[CH:35][C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=1)[C:14]1[C:9](=[CH:10][C:11]([O:18]C)=[CH:12][CH:13]=1)[CH:8]3[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:22][CH:21]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(S)C>ClCCCl>[OH:2][C:3]1[CH:36]=[CH:35][C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=1)[C:14]1[C:9](=[CH:10][C:11]([OH:18])=[CH:12][CH:13]=1)[CH:8]3[C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 15129665HCID 15129665, compound

Product 1

HCID 1512966711-{4-[2-(Piperidin-1-yl)ethoxy]phenyl}-11H-benzo[a]fluorene-3,9-diol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

One g of the compound of Example 11 was added to 1.9 g of aluminum chloride and 1.3 g of ethanethiol in 25 ml of 1,2-dichloroethane and the reaction was carried out and the product isolated as described in Example 14. One g of impure oily product was obtained, which was purified by Waters Prep 500 liquid chromatography over normal phase silica gel, using a gradient solvent which began with 2% methanol in chloroform and progressed to 30% methanol in chloroform. The product-containing fractions were evaporated to dryness under vacuum to obtain 0.7 g of the desired product as a tan foam.

Workup

  1. customthe product isolated
  2. customOne g of impure oily product was obtained
  3. customwhich was purified by Waters Prep 500 liquid chromatography over normal phase silica gel
  4. customThe product-containing fractions were evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-d75e82fa15594568b952d139b3b3c5b8
Source dataset
uspto-grants-1992_09
Patent number
US05147880

Reaction notes

Loading…