Lepidiline A → Lepidiline B

HRID 1815124Notes

Reaction equation

HRID 1815124 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N+:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]=1[CH3:21].[Cl-:22].[Br-].F[C:25]1C=CC(C[N+]2C(C)=C(C)N(CC3C=CC(F)=CC=3)C=2)=CC=1>CC(C)=O>[CH3:21][C:3]1[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]([CH3:25])=[N+:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]=1[CH3:1].[Cl-:22]

Participants

4

Reactant 2

HCID 404702Lepidiline A2×HCID 87974750HCID 87974750, compound

Product 1

HCID 9862174Lepidiline B

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The novel compound 1 was obtained as white needles in acetone, and its molecular formula of C19H19N2 was determined by HRFABMS. The IR spectrum of 1 showed a strong aromatic absorbance at 1560 cm−1. In 13C NMR spectrum of 1, only eight carbon signals were observed at δ 8.1 (q), 49.6 (t), 127.2 (s), 127.8 (d), 128.6 (d), 129.1 (d), 134.3 (s), and 135.5 (d), suggesting that the molecule of 1 is symmetrical to match the mass spectral data. Analysis of the 1H NMR signals at δ 5.41 (s), 7.31 (dd, J=8.8, 2.2 Hz), and 7.37-7.46 (m) and corresponding 13C NMR signals (gHMQC) at δ 49.6 (t), 127.8 (d), 128.6 (d), 129.1 (d), and 134.3 (s), indicated the appearance of a phenylmethylene group. This is supported by the COSY and gHMBC spectral data. A proton signal due to methyl group was observed as a singlet at δ 2.18, but the correlative carbon appeared in a very high field at δ 8.1 (q) in the gHMQC NMR experiment, similar to those of 1,3-di(4-fluorobenzyl)-4,5-dimethylimidazolium bromide, a synthesized product for the application as probes for intracellular pH determination. In the gHMBC NMR experiments of (1), the proton signal at 5.41 (s) exhibited other relevant cross-peaks at 127.2 (s) and 135.5 (d) attributable to C-2 and C-4 (5), respectively, apart from the ones of phenylmethylene moiety. On the other hand, H-2 showed two relevant cross-peaks at 49.6 (t) and 127.2 (s), assignable to the methylene group and C-4 (5), respectively.

Sources & evidence

ORD record
ord-2c56c36905d64fe8989f0adc34e73283
Source dataset
uspto-grants-2005_04
Patent number
US06878731B2

Reaction notes

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