HCID 66783001, compound → HCID 24954349, compound

HRID 1095576Notes

Reaction equation

HRID 1095576 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][C:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:5][CH2:4]1>Br.CCO>[CH3:29][N:2]([CH3:1])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 66783001HCID 66783001, compound

Product 1

HCID 24954349HCID 24954349, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 702EthanolSolvent

Procedure

(±)-4-[2-(4-Dimethylamino-4-phenylcyclohex-1-enyl)-1H-indol-3-yl]butan-1-ol (600 mg, 1.54 mmol) was dissolved in HBr/glacial acetic acid (33% HBr, 10 ml). Sn powder (1.81 g, 15.4 mmol) was then added to the mixture in portions at RT in the course of 2 h. When the addition had ended, the reaction mixture was stirred at RT for a further 16 h. For working up, the mixture was diluted with EtOH (10 ml) and concentrated to dryness on a rotary evaporator. The residue which remained was rendered basic by addition of 5 N NaOH (40 ml). The aqueous mixture obtained was extracted with methylene chloride (3×30 ml). The combined organic phases were dried over Na2SO4 and then concentrated. It was possible for the crude product obtained to be purified by column chromatography [silica gel 60 (50 g); MeOH (500 ml)]. 4-[2-(4-Dimethylamino-4-phenylcyclohexyl)-1H-indol-3-yl]butan-1-ol (less polar diastereomer) was obtained in a yield of 173 mg (29%) as a white solid.

Workup

  1. additionWhen the addition
  2. concentrationconcentrated to dryness on a rotary evaporator
  3. additionThe residue which remained was rendered basic by addition of 5 N NaOH (40 ml)
  4. customThe aqueous mixture obtained
  5. extractionwas extracted with methylene chloride (3×30 ml)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated
  8. customobtained
  9. customto be purified by column chromatography [silica gel 60 (50 g); MeOH (500 ml)]

Sources & evidence

ORD record
ord-19904f57e7744df38b5f3f38d2aa9224
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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