Cyclohexylamine → Cyclohexyl-(2-(4-pentylcyclohexyl)ethylidene)amine

HRID 1175561Notes

Reaction equation

HRID 1175561 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH:13]=O)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[CH:15]1([N:21]=[CH:13][CH2:12][CH:9]2[CH2:10][CH2:11][CH:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 11430Potassium CarbonateHCID 139990854-Pentylcyclohexaneacetaldehyde

Product 1

HCID 68430844Cyclohexyl-(2-(4-pentylcyclohexyl)ethylidene)amineYield 95.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(4-Pentylcyclohexyl)acetaldehyde (30.1 g) was dissolved in diethyl ether (40 mL), to which cyclohexylamine (15.2 g) and potassium carbonate (12 g) were added, and the system was stirred at room temperature over night. The resulting suspension was filtered with Celite, and the filtrate was concentrated under reduced pressure. Cyclohexyl-(2-(4-pentylcyclohexyl)ethylidene)amine (40.6 g) in a yellow oily form thus obtained was used in the second step without purification.

Workup

  1. additionwere added
  2. filtrationThe resulting suspension was filtered with Celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d7213c02cd1946a494a3bc8613fb3f9f
Source dataset
uspto-grants-2010_11
Patent number
US07842357B2

Reaction notes

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