Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions

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This journal is The Royal Society of Chemistry 213 Synthesis of Imines from

Wenjing Cui, a Bao Zhaorigetu,* a Meilin Jia, a and Wulan Ao, a Huaiyong

(a) TEM images and (b) size distribution of the 1%wtPd/ZrO 2 catalysts.

1 This journal is The Royal Society of Chemistry 213 Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions Wenjing Cui, a Bao Zhaorigetu,* a Meilin Jia, a and Wulan Ao, a Huaiyong Zhu b Figure S1. (a) TEM images and (b) size distribution of the 1%wtPd/ZrO 2 catalysts. Figure S2. XRD pattern of (a) 1 wt% Pd/ZrO 2 catalysts and (b) ZrO 2 Figure S3. X-ray photoelectron spectrum (XPS) of Pd 3d in 1 wt% Pd/ZrO 2

2 This journal is The Royal Society of Chemistry 213 Figure S4. Recyclability tests of Pd/ZrO 2 for the synthesis of imine from benzylamine and ethanol Table S1 The reaction of benzylamine with aliphatic alcohols on different catalysts a Yield (%) b Entry Aliphatic Alcohol 3 wt% Au/ZrO 2 3 wt% Pd/ZrO 2 3 wt% Au-Pd/ZrO 2 1 CH 3 OH(2b) a CH 3 (CH 2 ) 2 OH(2c) CH 3 (CH 2 ) 3 OH(2d) CH 3 (CH 2 ) 4 OH(2e) CH 3 (CH 2 ) OH(2f) OH(2g) OH(2h) OH(2i) (76) c 1 OH (2j) OH (2k) C OH (2l) a Reaction conditions: 1 (1 mmol), 2 (1 ml), catalyst (1 mg), KOH (.1 mmol), air atmosphere, 3 C, 6h; b determined by GC; c reaction time 12 h.

3 This journal is The Royal Society of Chemistry 213 Experimental General. The mixture of amine 1a (1 mmol), alcohol 2a (1 ml), 1 wt% Pd/ZrO 2 (1 mg) and KOH (.1 mmol) was sealed under air in a ml tube, stirred at 3 C for 6 h. During the reactions.1 ml specimens were periodically sampled, filtered and analyzed by GC (Shimadzu GC-214) with a capillary column of Rtx- (3 m length,. mm internal diameter,. μm film thickness), temperature of column ranged from to 22 C (6 C/min), and injector temperature was 2 C and flame ionization detector was used for product analysis. All synthetic compounds are known, and they were identified by comparison with authentic samples. Selected products were purified by column chromatography on alumina gel (V petroleum ether: V ethyl acetate: V triethylamine was : 1: 1), and were analyzed by 1 H NMR. We compared their 1 H NMR spectra with the reported literature. GC-MS (Thermo DSQ Ⅱ) with a HP- column was also used to identify the products. Characterization of products and Rerference N-ethylidenebenzylamine Product 3aa (CAS registry No: ) 1 H NMR ( MHz, MeOD) δ 7.74 (t, J =.2 Hz, 1H), (m, H), 4.4 (s, 2H), 1.86 (dt, 3H) ppm. This compound was known: F. Texier-Boullet, Synthesis, 198, N-propylidenebenzylamine Product 3ac (CAS registry No: ): 1 H NMR ( MHz, MeOD) δ 7.82 (t, J =.2 Hz, 1H), (m, H), 4.3 (s, 2H), (m, 2H), (m, 2H),.96 (t, J = 7.4 Hz, 3H) ppm. This compound was known: V. Coeffard, C. Thobie-Gautier, I. Beaudet, Eur. J. Org. Chem., 28, N-butylidenebenzylamine Product 3ad (CAS registry No: ) 1 H NMR ( MHz, MeOD) δ 7.94 (t, 1H), (m, H), 4.4(s, 2H), 2.7 (td, J = 7., 1.2

4 This journal is The Royal Society of Chemistry 213 Hz, 2H), 1.71 (dt, J = 14., 7.2 Hz, 2H),.9 (t, J = 7.4 Hz, 3H). This compound was known: P. K. Khatri, S. L. Jain, L. N. Sivakumar K, Org. Biomol. Chem., 211, 9, Results of GC-MS: 3aa D #312- RT: AV: 94 NL:.3E ab A #2 RT: 3.84 AV: 1 NL: 8.22E ac

5 This journal is The Royal Society of Chemistry 213 A # RT: AV: 113 NL: 2.61E ad F #748 RT: 6.17 AV: 1 NL: 1.2E

6 This journal is The Royal Society of Chemistry 213 3ae O #962 RT: 7.8 AV: 1 NL: 2.27E af I #1324 RT: 8.61 AV: 1 NL: 3.26E

7 This journal is The Royal Society of Chemistry 213 3ag C #-629 RT: AV: NL: 9.79E8.9 3ah #818 RT: 6.47 AV: 1 NL: 1.E

8 This journal is The Royal Society of Chemistry 213 3ai E #4-616 RT:.-.61 AV: 63 NL: 4.1E aj B # RT: AV: 187 NL: 2.34E

9 This journal is The Royal Society of Chemistry 213 3ak C #961 RT: 7.7 AV: 1 NL: 8.28E ba W #6 RT:.99 AV: 1 NL: 2.34E

10 This journal is The Royal Society of Chemistry 213 3ca 1 #2 RT:.2 AV: 1 NL: 1.E da V #869 RT: 6.68 AV: 1 NL: 7.3E ea X #837 RT: 6.4 AV: 1 NL: 3.3E

11 This journal is The Royal Society of Chemistry 213 3fa 9 #7 RT: 6.24 AV: 1 NL: 4.E ga T #433 RT: 4.83 AV: 1 NL: 4.E ha Y #347 RT: 4.47 AV: 1 NL: 6.8E

12 This journal is The Royal Society of Chemistry 213 3ia U #2188 RT: AV: 1 NL: 1.22E

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