Cyclohexylamine → HCID 4344263, compound

HRID 1243665Notes

Reaction equation

[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:8][C:9]([F:24])([F:23])[C:10]1[CH:11]=[C:12]([N:20]=[C:21]=[O:22])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1>ClCCl>[CH:1]1([NH:7][C:21]([NH:20][C:12]2[CH:13]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:15]=[C:10]([C:9]([F:8])([F:23])[F:24])[CH:11]=2)=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

Cyclohexylamine 4.98 g (49.3 mmol) was added to 120 ml of anhydrous dichloromethane in a 500 ml round bottomed flask. This stirred solution was cooled to 0° C. using an ice water bath. 3,5-Bis(trifluoromethyl)phenyl isocyanate 12.33 g (48.3 mmol) was added drop wise over a period of 15 minutes. The reaction mixture was allowed to warm to room temperature and stirred at ambient temperatures for 18 hours. During this time a heavy precipitate was formed. This solid was collected by filtration on a Buchner funnel, and was re-suspended in 250 ml of dichloromethane. After approximately 30 minutes of stirring, the solid was again filtered on a Buchner funnel and then placed under vacuum at 40° C. to dry for a period of 24 hours to give 15.4 g of a white solid (90% yield). 1H NMR (400 MHz DMSO) δ 9.10 (s 1H) 8.10 (s 2H) 7.53 (s 1H) 6.43 (d 1H) 3.49 (m 1H) 1.81 (t 2H) 1.68 (m 2H) 1.54 (m 1H) 1.25 (m 5H). MS: m/z 355 (M+1).

Workup

temperatureto warm to room temperature
customDuring this time a heavy precipitate was formed
filtrationThis solid was collected by filtration on a Buchner funnel
stirringAfter approximately 30 minutes of stirring
filtrationthe solid was again filtered on a Buchner funnel
customplaced under vacuum at 40° C.
customto dry for a period of 24 hours

Sources & evidence

ORD record: ord-59290ebf99f449a79cfe1b7459118a16
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119120B2

Reaction notes

Loading…