Hydrochloric Acid → HCID 178448796, compound

HRID 386981Notes

Reaction equation

HRID 386981 reaction equation
[CH2:1](/[N:5]=[C:6]1\[CH2:7][CH2:8][CH2:9][CH:10]=[C:11]\1[NH:12][C:13]1[C:18]([CH:19]([CH3:21])[CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=1[CH:22]([CH3:24])[CH3:23])[CH2:2][CH2:3][CH3:4].C1(C)C=CC=CC=1.Cl>C(OCC)C>[CH:22]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]([CH3:20])[CH3:21])[C:13]=1/[N:12]=[C:11]1/[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH2:8][CH2:9][CH2:10]/1)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 178448797HCID 178448797, compound

Product 1

HCID 178448796HCID 178448796, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Charge a vial with N-((6E)-6-(butylimino)-1-cyclohexen-1-yl)-2,6-bis(1-methylethyl)-benzenamine (B) (3.0038 g, 9.1995 mmol, Example B) and toluene (30.0 mL). Stir the resulting yellow solution and add a solution of 1.0M HCl (aqueous, 0.46 mL, 0.46 mmol) in diethyl ether. Stir the resulting reaction mixture for 3 hours. To the mixture add hexanes (5 mL) and filter (syringe filter) to remove fine solids. Wash the filtered solids with hexanes (6 mL), and concentrate the filtrate overnight under reduced pressure to give 3.0107 g of the product (L)d as a thick brown oil.

Workup

  1. stirringStir
  2. customthe resulting reaction mixture for 3 hours
  3. filtrationfilter
  4. filtration(syringe filter)
  5. customto remove fine solids
  6. washWash the filtered solids with hexanes (6 mL)
  7. concentrationconcentrate the filtrate overnight under reduced pressure

Sources & evidence

ORD record
ord-e9ba5aba0d174c928d2e3bad192f44d1
Source dataset
uspto-grants-2013_02
Patent number
US08372927B2

Reaction notes

Loading…