4-(Trifluoromethyl)aniline → HCID 86709740, compound

HRID 2174606Notes

Reaction equation

HRID 2174606 reaction equation
[C:1]1([C@@H:7]2[C:9]3([CH2:13][CH2:12][CH2:11][CH2:10]3)[C@H:8]2[C:14]([OH:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:17][C:18]([F:27])([F:26])[C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1>>[C:1]1([C@@H:7]2[C:9]3([CH2:10][CH2:11][CH2:12][CH2:13]3)[C@H:8]2[C:14]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([C:18]([F:17])([F:26])[F:27])=[CH:20][CH:21]=2)=[O:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 86709739HCID 86709739, compound

Product 1

HCID 86709740HCID 86709740, compoundYield 60.1%

Procedure

trans-2-Phenylspiro[2.4]heptane-1-carboxylic acid (300 mg, 1.39 mmol) and 4-trifluoromethyl-phenylamine (224 mg, 1.39 mmol) were reacted as described under General Procedure D to furnish the title compound (300 mg, 60%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.69 (d, J=8.8 Hz, 2H), 7.58-7.52 (m, 3H), 7.33-7.20 (m, 3H), 7.15-7.12 (m, 2H), 2.92 (d, J=5.5 Hz, 1H), 2.06 (d, J=5.5 Hz, 1H), 1.93-1.91 (m, 2H), 1.73-1.60 (m, 4H), 1.52-1.40 (m, 2H). mp 171-173° C. ESIMS m/z [M+H]+ 360.2.

Sources & evidence

ORD record
ord-15bca8c8ed6e4db5abc8a35d88b4ffe1
Source dataset
uspto-grants-2015_06
Patent number
US09062013B2

Reaction notes

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