HCID 57475181, compound → 1-Benzyl-4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine

HRID 1095595Notes

Reaction equation

HRID 1095595 reaction equation
[CH2:1]([C:8]1([N:26]([CH3:28])[CH3:27])[CH2:13][CH2:12][C:11]([C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[CH:18][CH:17]=3)=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br.CCO.C(OCC)(=O)C>[CH2:1]([C:8]1([N:26]([CH3:28])[CH3:27])[CH2:9][CH2:10][CH:11]([C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[CH:18][CH:17]=3)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 57475181HCID 57475181, compound

Product 1

HCID 667829431-Benzyl-4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(±)-N-[1-Benzyl-4-(5-methoxy-3-methyl-1H-indol-2-yl)cyclohex-3-enyl]-N,N-dimethylamine (1.97 g, 5.26 mmol) was suspended in HBr/glacial acetic acid (33% HBr, 30 ml). Sn powder (3.12 g, 26.3 mmol) was then added to the mixture in portions in the course of 30 min. When the addition had ended, the reaction mixture was stirred at RT for a further 48 h.—For working up, the mixture was diluted with EtOH (20 ml) and concentrated to dryness on a rotary evaporator. The residue which remained was rendered basic by addition of 5 N NaOH (100 ml). The aqueous mixture obtained was extracted with methylene chloride (4×20 ml). The combined organic phases were washed with water (50 ml), dried over Na2SO4 and then concentrated. The residue obtained (1.7 g) was dissolved in ethyl acetate (10 ml). The mixture was placed in a refrigerator for 2 h for crystallization. 1-Benzyl-4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine (less polar diastereoisomer) was separated off by filtration in a yield of 500 mg (25%) as a beige solid. The mother liquor was concentrated and the residue was purified by column chromatography [silica gel 60 G (150 g); EtOAc (1,000 ml)]. The polar product was obtained in a yield of 134 mg (7%) as a brown oil.

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 (100 ml)
  4. customThe aqueous mixture obtained
  5. extractionwas extracted with methylene chloride (4×20 ml)
  6. washThe combined organic phases were washed with water (50 ml)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue obtained (1.7 g)
  10. customThe mixture was placed in a refrigerator for 2 h for crystallization
  11. custom1-Benzyl-4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine (less polar diastereoisomer) was separated off by filtration in a yield of 500 mg (25%) as a beige solid
  12. concentrationThe mother liquor was concentrated
  13. customthe residue was purified by column chromatography [silica gel 60 G (150 g); EtOAc (1,000 ml)]
  14. customThe polar product was obtained in a yield of 134 mg (7%) as a brown oil

Sources & evidence

ORD record
ord-b405d9b3563f4e24a2bc027f88ce978e
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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