Toluene → HCID 178420343, compound

HRID 2200012Notes

Reaction equation

HRID 2200012 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([CH3:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C=O)CCC=CC1>O>[CH:2]1(/[CH:1]=[N:8]/[CH2:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7504BenzylamineHCID 75083-Cyclohexene-1-carboxaldehyde

Product 1

HCID 178420343HCID 178420343, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
112.5 °C

Procedure

To a flask equipped with a Dean-Stark apparatus was added benzylamine (B) (97.3 g, 0.91 mol) and toluene (350 g). The mixture was warmed to 110-115° C. and 3-cyclohexene-1-carboxaldehyde (A) (100 g, 0.91 mol) was added over 1-1.5 h, while azeotropically removing water. After the addition was complete, toluene was distilled (approx. 100 mL) and then the reaction was cooled to 20-30° C. The resulting solution was approximately 40 w/w % (1) in toluene. The solution of (1) in toluene was carried forward without further isolation or purification. Typical assay: 99 area % purity (GC), retention time 15.3 min. 1H NMR (400 MHz, CDCl3) δ 7.78-7.75 (1H, m), 7.37-7.32 (2H, m), 7.30-7.26 (3H, m), 5.75-5.73 (2H, m), 4.62 (2H, s), 2.62-2.52 (1H, m), 2.31-2.23 (1H, m), 2.20-2.11 (3H, m), 2.00-1.93 (1H, m), 1.68-1.58 (1H, m).

Workup

  1. customTo a flask equipped with a Dean-Stark apparatus
  2. additionAfter the addition
  3. distillationtoluene was distilled (approx. 100 mL)
  4. temperaturethe reaction was cooled to 20-30° C
  5. customThe solution of (1) in toluene was carried forward without further isolation or purification

Sources & evidence

ORD record
ord-5749e656cb894c00ac920390d4d77cb8
Source dataset
uspto-grants-2016_06
Patent number
US09359356B2

Reaction notes

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