Hydrochloric Acid → HCID 68828835, compound

HRID 1786512Notes

Reaction equation

HRID 1786512 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]=[CH:12][CH:13]2[CH2:18][CH2:17][C:16]([N:25]([CH3:27])[CH3:26])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[CH:2]1.[Cl:28][Si](C)(C)C.C(OCC)C.Cl>CC(=O)CC>[ClH:28].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]=[CH:12][CH:13]2[CH2:18][CH2:17][C:16]([N:25]([CH3:27])[CH3:26])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 68828836HCID 68828836, compound2×

Product 1

HCID 68828835HCID 68828835, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

As described for Example 8, less polar diastereoisomers of {4-[3-(1H-indol-3-yl)-propenyl]-1-phenylcyclohexyl}dimethylamine were not obtained cleanly. For purification, 750 mg non-polar crude product were suspended in 95 ml water and 1 ml 85% by weight phosphoric acid. The suspension was shaken with diethyl ether (3×20 ml), the diethyl ether was decanted off in each case and the solid subsequently suction filtered and washed with diethyl ether (10×3 ml). The solid was dried, dissolved in DMF and 1M NaOH (10 ml) added. The alkaline solution was extracted with EE (5×10 ml). The combined EE phases were dried, filtered and evaporated. The residue obtained, 309 mg of a less polar diastereoisomer of {4-[3-(1H-indol-3-yl)-propenyl]-1-phenylcyclohexyl}dimethylamine (viscous oil), was dissolved in 2-butanone (5 ml), and subsequently chlorotrimethylsilane (0.33 ml, 2.6 mmole) was added and the mixture stirred overnight at RT. After adding diethyl ether (3 ml) and a further 30 min, the precipitated hydrochloride of a less polar diastereoisomer of 4-[3-(1H-indol-3-yl)-propenyl]-1-phenylcyclohexyl}dimethylamine was suction filtered and isolated in a yield of 137 mg (beige solid, mp. 138 to 142° C.).

Workup

  1. customwere not obtained cleanly
  2. customFor purification, 750 mg non-polar crude product
  3. customthe diethyl ether was decanted off in each case
  4. filtrationthe solid subsequently suction filtered
  5. washwashed with diethyl ether (10×3 ml)
  6. customThe solid was dried
  7. dissolutiondissolved in DMF
  8. addition1M NaOH (10 ml) added
  9. extractionThe alkaline solution was extracted with EE (5×10 ml)
  10. customThe combined EE phases were dried
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue obtained
  14. stirringthe mixture stirred overnight at RT
  15. customa further 30 min
  16. filtrationfiltered
  17. customisolated in a yield of 137 mg (beige solid, mp. 138 to 142° C.)

Sources & evidence

ORD record
ord-b389fc697dc240099ed29c4eb07b7eba
Source dataset
uspto-grants-2009_03
Patent number
US07507758B2

Reaction notes

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