Cyclohexylamine → HCID 178424359, compound

HRID 409611Notes

Reaction equation

HRID 409611 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]C[CH:2]1C=O.[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH3:20][CH2:21][CH2:22]CCC>CO>[NH:19]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][C:14]=2/[CH:2]=[N:1]/[CH:10]2[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]2[CH3:4])[CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8058HexaneHCID 19358683HCID 19358683, compound

Product 1

HCID 178424359HCID 178424359, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.06 g of tetrahydroquinolino aldehyde was dissolved in 17 ml of methanol and then 1.3 ml of cyclohexyl amine was slowly added thereto. After the mixture was stirred at room temperature overnight, the solvent was eliminated under a reduced pressure and the resulting product was dissolved again in hexane to provide a thick solution, which was then kept in a freezer. In this solution, two types of stereomeric products were mixed at a ratio of 1.5:1. After the solution was left alone for about two days, a white crystalline solid product was found to be formed. The same procedures were repeated with the remaining mother liquor and all of the solid products thus obtained were collected and washed with cold methanol and hexane, and then dried to provide a pure stereomeric product. (Yield: 50%)

Workup

  1. customto provide a thick solution, which
  2. additionIn this solution, two types of stereomeric products were mixed at a ratio of 1.5:1
  3. waitAfter the solution was left alone for about two days
  4. customto be formed
  5. customall of the solid products thus obtained
  6. customwere collected
  7. washwashed with cold methanol and hexane
  8. customdried
  9. customto provide a pure stereomeric product

Sources & evidence

ORD record
ord-233ff89c175a4368988e3f9b20753b9c
Source dataset
uspto-grants-2014_06
Patent number
US08759461B2

Reaction notes

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