Methanol → HCID 178424359, compound

HRID 574989Notes

Reaction equation

HRID 574989 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1C=O.[CH3:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[NH2:20].[CH3:21]O>>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2/[CH:21]=[N:20]/[CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]2[CH3:13])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 234322-MethylcyclohexylamineHCID 19358683HCID 19358683, compound

Product 1

HCID 178424359HCID 178424359, compoundYield 50%

Procedure

1.06 g of tetrahydroquinolino aldehyde was dissolved in 17 mL of methanol, and 1.3 mL of 2-methylcyclohexyl amine was slowly added. After agitated overnight at the room temperature, the resultant solution was removed of the solvent under reduced pressure and then dissolved in hexane again to prepare a thick solution, which was stored in a freezer. This solution contained two stereoscopic isomer products at a ratio of about 1.5:1. After about 2 days, a white crystalline solid appeared in the solution. The same procedures were performed on the remaining store solution to collect a solid, which was washed with cold methanol and hexane and dried to yield pure stereoscopic isomer products (yield: 50%).

Workup

  1. customthe resultant solution was removed of the solvent under reduced pressure
  2. dissolutiondissolved in hexane again
  3. customto prepare a thick solution, which
  4. waitAfter about 2 days
  5. customto collect a solid, which
  6. washwas washed with cold methanol and hexane
  7. customdried

Sources & evidence

ORD record
ord-884214d9c28649799036bbbe65b35ef4
Source dataset
uspto-grants-2015_05
Patent number
US09035006B2

Reaction notes

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