HCID 57475045, compound → HCID 24953296, compound

HRID 1095553Notes

Reaction equation

HRID 1095553 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:7][C:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH3:18])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:5][CH2:4]1>Br>[CH3:25][N:2]([CH3:1])[C:3]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:4][CH2:5][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH3:18])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:7][CH2:8]1

Participants

3

Reactant 1

HCID 57475045HCID 57475045, compound

Product 1

HCID 24953296HCID 24953296, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

(±)-N,N-Dimethyl-N-[4-(3-methyl-1H-indol-2-yl)-1-phenylcyclohex-3-enyl]amine (550 mg, 1.66 mmol) were dissolved in HBr/glacial acetic acid (33% HBr, 20 ml). Sn powder (1 g, 8.5 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 for a further 30 min.—For working up, the mixture was concentrated to dryness on a rotary evaporator. The residue which remained was rendered basic by addition of 2N NaOH (20 ml). The aqueous mixture obtained was extracted with ethyl acetate (4×20 ml). The combined organic phases were dried with Na2SO4 and then concentrated. The residue obtained (530 mg) was recrystallized from methanol (60 ml). N,N-Dimethyl-N-[4-(3-methyl-1H-indol-2-yl)-1-phenylcyclohexyl]amine (less polar isomer) was obtained in this way in a yield of 222 mg (40%, melting point: from 204° 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 2N NaOH (20 ml)
  4. customThe aqueous mixture obtained
  5. extractionwas extracted with ethyl acetate (4×20 ml)
  6. dry with materialThe combined organic phases were dried with Na2SO4
  7. concentrationconcentrated
  8. customThe residue obtained (530 mg)
  9. customwas recrystallized from methanol (60 ml)

Sources & evidence

ORD record
ord-5e630dea3ec048ba9054543a83e91c96
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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