HCID 66782859, compound → HCID 24953992, compound

HRID 1095557Notes

Reaction equation

HRID 1095557 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:8][CH2:7][C:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH3:18])=[CH:15][C:14]([F:19])=[CH:13][CH:12]=3)=[CH:5][CH2:4]1>Br.C(O)C>[F:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH:6]1[CH2:7][CH2:8][C:3]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([N:2]([CH3:26])[CH3:1])[CH2:4][CH2:5]1)=[C:17]2[CH3:18]

Participants

4

Reactant 1

HCID 66782859HCID 66782859, compound

Product 1

HCID 24953992HCID 24953992, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 702EthanolSolvent

Procedure

(±)-2-(4-(Dimethylamino)-4-phenylcyclohex-1-enyl)-3-methyl-5-fluoro-1H-indole (free base from Example 28) (420 mg, 1.2 mmol) was dissolved in HBr/glacial acetic acid (33% HBr, 25 ml). Sn powder (1.4 g, 12 mmol) was then added to the mixture in portions in the course of 40 min. When the addition had ended, the reaction mixture was stirred for a further 60 min.—For working up, the mixture was concentrated to dryness on a rotary evaporator. The residue which remained was rendered basic by addition of 5 N NaOH (40 ml). Methylene chloride was added to the solution obtained and the mixture was extracted (4×20 ml). The combined organic phases were dried with MgSO4 and then concentrated. The residue obtained (360 mg) was boiled up in ethanol (30 ml), the substance only partly dissolving. The mixture was left at 5° C. for 1 h and the solid was then separated off. 4-(5-Fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine (less polar isomer) was obtained in this way in a yield of 256 mg (60%, melting point: 199-205° C.).

Workup

  1. additionWhen the addition
  2. concentrationthe mixture was concentrated to dryness on a rotary evaporator
  3. additionThe residue which remained was rendered basic by addition of 5 N NaOH (40 ml)
  4. additionMethylene chloride was added to the solution
  5. customobtained
  6. extractionthe mixture was extracted (4×20 ml)
  7. dry with materialThe combined organic phases were dried with MgSO4
  8. concentrationconcentrated
  9. customThe residue obtained (360 mg)
  10. dissolutionthe substance only partly dissolving
  11. waitThe mixture was left at 5° C. for 1 h
  12. customthe solid was then separated off

Sources & evidence

ORD record
ord-2871b030a07b43c484b4aa5af12245d1
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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