Trifluoroacetic acid → HCID 9839386, compound

HRID 1391990Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:24]([CH3:30])=[C:25]([C:28]#[N:29])[C:26]#[N:27])[CH:20]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[N:11]1([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[CH:20]=[C:19]([C:24](=[C:25]([C:26]#[N:27])[C:28]#[N:29])[CH3:30])[CH:18]=[CH:17]3)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 15398672HCID 15398672, compound

Product 1

HCID 9839386HCID 9839386, compound

Procedure

When tert-butyl-4-[6-(2,2-dicyano-1-methylvinyl)-2-naphthyl]-1-piperazinecarboxylate was treated with TFA (trifluoroacetic acid) at room temperature, TLC showed that the reaction was over in 5 minutes and gave a single product, 2-[1-(6-piperazino-2-naphthyl)ethylidene]malononitrile. The TFA was removed in vacuo at room temperature. 1H NMR: δ 2.72 (s, 3H, CH3), 3.50 and 3.63 (broad, 8H, piperazine), 7.18 (broad s, 1H, 5-H), 7.29 (d, 1H, 7-H), 7.59 (d, 1H, 3-H), 7.79 (d, 1H, 4-H), 7.87 (d, 1H, 8-H), 8.04 (s, 1H, I—H), 9.0 (broad, 1.5H, NH and acid); J7,8=8.8 Hz, J3,4=8.4 Hz. 19F NMR: δ −76.2 (CF3COO).

Workup

customwas over in 5 minutes

Sources & evidence

ORD record: ord-ccdfd5081d334f7a8b1169ee3c593be4
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07341709B2

Reaction notes

Loading…