Aniline → HCID 11961746, compound

HRID 1006728Notes

Reaction equation

[CH2:1]([CH:16]1[CH2:21][CH2:20][CH2:19][C:18](=O)[CH2:17]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].Cl.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>ClCCl>[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:18]2([C:35]3[CH:36]=[CH:37][C:32]([NH2:31])=[CH:33][CH:34]=3)[CH2:19][CH2:20][CH2:21][CH:16]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:17]2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A 100 mL single necked flask fitted with a magnetic stirrer and a reflux condenser was charged with a 10.0 g (32 mmol) of 3-pentadecylcyclohexanone, 8.4 g (65 mmol) aniline hydrochloride and 12.05 g (130 mmol) of aniline. The resulting mixture was refluxed at 140° C. for 10 hours under positive pressure of nitrogen. The reaction mixture was cooled to room temperature, diluted with dichloromethane, and washed with aqueous sodium hydroxide solution and water and dried over sodium sulfate. Solvent was distilled off and excess aniline removed under vacuum. The desired 1,1-bis(4-aminophenyl)-3-pentadecylcyclohexan was obtained in a yield of 5.4 g (35% of theoretical). M.p. 107° C.

Workup

customA 100 mL single necked flask fitted with a magnetic stirrer and a reflux condenser
temperatureThe reaction mixture was cooled to room temperature
washwashed with aqueous sodium hydroxide solution and water
dry with materialdried over sodium sulfate
distillationSolvent was distilled off
customexcess aniline removed under vacuum

Sources & evidence

ORD record: ord-f523c9ecfe2242ddbfe982e63221ae16
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790993B1

Reaction notes

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