1-Phenethylamine, (-)- → HCID 54494501, compound

HRID 1108761Notes

Reaction equation

HRID 1108761 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[C:16]1([C@@H:22]([NH2:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H][H]>[Ni].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH:24][CH:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:23])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 758181-Phenethylamine, (-)-HCID 12039786HCID 12039786, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54494501HCID 54494501, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel (0.5 g) was added to a solution of 3-(3-methoxyphenyl)cyclohexanone (2.05 g) and (S)-1-phenylethylamine (1.22 g) in ethanol (20 ml) prior to room temperature stirring and hydrogen addition. After the starting materials were consumed, the catalyst was filtered off, and the filtrate was distilled off under reduced pressure to produce a light yellow oily substance which was then separated and purified by silica gel column chromatography (chloroform:methanol=50:1) to give 1.62 g of N-[3-(3-methoxyphenyl) cyclohexyl]-N-(1-phenylethyl)amine (a mixture of trans-H form and trans-L form) (52.5% yield). The proportion of trans form to cis form with this reaction was about 12 to 1 (confirmed by HPLC) . Repeated column chromatography enabled separation of trans-H and trans-L.

Workup

  1. customAfter the starting materials were consumed
  2. filtrationthe catalyst was filtered off
  3. distillationthe filtrate was distilled off under reduced pressure
  4. customto produce a light yellow oily substance which
  5. customwas then separated
  6. custompurified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-460cc2e449f046e29be20c285ccd8f07
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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