Composition and reactivity of aminolysis products of phenyl glycidyl ether with benzylamine

Article abstract of DOI:10.1134/S1070428017050037

Composition of aminolysis products of phenyl glycidyl ether with benzylamine in various conditions was studied. The ratio of 1-(benzylamino)-3-phenoxypropan-2-ol and 1,1'-(benzylazanediyl)bis(3-phenoxypropan-2-ol) does not considerably depend on the nature of the solvent and is basically determined by ratio of initial reagents. 2,6-Bis(phenoxymethyl)morpholine was obtained by dehydration of aminodiol in conditions of Mitsunobu reaction with subsequent reductive debenzylation.

Full text of DOI:10.1134/S1070428017050037

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2017, Vol. 53, No. 5, pp. 656–662. © Pleiades Publishing, Ltd., 2017.
Original Russian Text © V.А. Pal’chikov, S.Yu. Mykolenko, А.N. Pugach, F.I. Zubkov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53,
No. 5, pp. 651–656.
Composition and Reactivity of Aminolysis Products Glycidyl
of Phenyl Ether with Benzylamine
V. А. Pal’chikova,* S. Yu. Mykolenkob, А. N. Pugachb, and F. I. Zubkovc
a Oles’Honchar Dnepropetrovsk National University, pr. Gagarina 72, Dnepropetrovsk, 49010 Ukraine
*e-mail: palchikoff@mail.ru
b Dnepropetrovsk State Agrarian and Economic University, Dnepropetrovsk, Ukraine
c RUDN University, Moscow, Russia
Received January 11, 2017
Abstract—Composition of aminolysis products of phenyl glycidyl ether with benzylamine in various
conditions was studied. The ratio of 1-(benzylamino)-3-phenoxypropan-2-ol and 1,1'-(benzylazanediyl)bis(3-
phenoxypropan-2-ol) does not considerably depend on the nature of the solvent and is basically determined by
ratio of initial reagents. 2,6-Bis(phenoxymethyl)morpholine was obtained by dehydration of aminodiol in
conditions of Mitsunobu reaction with subsequent reductive debenzylation.
DOI: 10.1134/S1070428017050037
Interest to the chemistry of 2,3-epoxypropyl
(glycidyl) derivatives is due to the multitude of β-
adrenoblockers that found wide application mainly in
therapy of cardiovascular diseases (hypertonia,
arrhythmia, cardiomyopathy, ischemic heart disease)
and by chemical nature belong to amino and hydroxy
derivatives of aryl glycidyl ethers (propanolol,
atenolol, atenol, metoprolol, betaxolol, acebutolol,
nipradilol, nadolol, carazolol, pindolol, nebivolol, etc.)
[1–4]. Amino alcohols obtained from 2,3-epoxypropyl
ethers, and their derivatives possess antiviral,
antibacterial, and tuberculocidal action [5]. Among
these compounds antibiotics, antiarrhythmic, and
antihyperglycemic substances [6, 7], drugs against
osteoporosis [8], and antidepressants [9] were
discovered.
Previously we demonstrated that the reaction of
aryl glycidyl ethers 1 with equimolar amount of
(bicyclo[2.2.1]hept-5-en-endo-2-yl)methylamine 2 in
2-propanol resulted in mixtures of amino alcohols 3
and amino dioles 4 (Scheme 1) [10–12]. Yet amino
dioles were not present in reaction products of amine 2
with other epoxides [epoxycyclohexane, 4-nitro-
phenyloxirane, N-(2,3-epoxypropyl)carbazole, N-(2,3-
epoxypropyl)camphorimide, N-(2,3-epoxypropyl)aryl-
sulfonamides] [13–19].
To reveal the features of reactions between the
scaffold amine 2 and aryl glycidyl ethers we
investigated the ratio of products of model reaction
between phenyl glycidyl ether 5 with benzylamine,
taken as a simple model of amine 2 (Scheme 2). The
Scheme 1.
OAr
i-PrOH, 20oC
O
+
+
N
OAr
N
OAr
OH
NH2
H
ArO
2
1
OH
OH
3, 52_81%
4, 19_48%
656

COMPOSITION AND REACTIVITY OF AMINOLYSIS PRODUCTS OF PHENYL GLYCIDYL
657
Scheme 2.
OH
Bn
N
OH
O
Bn
OH
O
NH2
N
H
+
+
OPh
OPh
OPh
5
6
7
latest data [20–28] and the results of our investigations
of this reaction in different solvents with different
ratios of initial reagents are presented in the table. The
ratio of reaction products 6 and 7 in the reaction
mixture was evaluated by chromato-mass-spectrometry
method (LCMS) by peaks that corresponded to
Effect of conditions of aminolysis of epoxide 5 with benzylamine on yields of aminoalcohol 6 and aminodiol 7
Yield, %
Reaction conditions
Molar ratio epoxide-amine
Reference
6
7
–
Zn(ClO4)2–Al2O3, CH2Cl2, 2.5 h, 20°C
Ca(OTf)2, MeCN, 5 h, 20°C
Sulfated Zirconia, 0.5 h, solvent-free, 60°C
Mg(ClO4)2, solvent-free, 5 h, 20°C
Graphite oxide, solvent-free, 20°C, 15 min
6 h, 20°C, 2,2,2-Trifluorethanol
Sulfated Zirconia, 0.33 h, solvent-free, 60°C, MW
β-Cyclodextrine
1 : 1
1 : 1
1 : 1.1
1 : 1.05
1 : 1
1 : 1
1 : 1.1
1 : 1
1 : 1
1 : 1
1 : 1
1 : 1
1 : 1
1 : 1
1 : 1
1 : 1
1 : 1
1 : 1
1 : 1
1 : 2
1 : 5
2 : 1
88
87
87
87
87
85
83
75
70
63
73
61
59
58
62
66
56
58
68
86
95
0
[20]
[21]
–
–
[22]
–
[23]
–
[24]
–
[25]
–
[26]
–
[27]
PhMe, reflux, 16 h
–
[28]
H2O (PI 9.0)a
37
27
39
41
42
38
34
44
42
32
14
5
Our datab
MeCN (PI 5.8)
MeOH (PI 5.1)
THF (PI 4.0)
i-PrOH (PI 3.9)
CH2Cl2 (PI 3.1)
Et2O (PI 2.8)
PhMe (PI 2.4)
C6H14 (PI 0.0)
Solvent-free
i-PrOH
i-PrOH
i-PrOH
100
а
PI (Polarity Index) is solvent polarity index.
All reactions were performed at 25°C (stirring for 24 h).
b
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 5 2017

PAL’CHIKOV et al.
658
Scheme 3.
H
O
1.009
H
0.993
1.767
H
Ph
H
O
O
CH2
CH
1.669
2.066
2.472
O
1.397
1.877
1.394
H
O
H
1.46
1
1.01
9
CH2 1.472
2.108
1.026
1.686
CH
2.1
03
1.858
CH2
CH2
N
CH2
CH2
O
N
H
1.026
1.0
07
H
1.907
Ph
2.062
CH2
O
1.79
0
0.976H
O
O0.992H
CH
CH2
H
H
Ph
O
TS1
TS2
characteristic signals, m/z 258 [M + Н]+ (6) and 408
[M + Н]+ (7).
opening of glycidyl ethers under the action of amine 2
should be connected with additional stabilization of
transition states TS1 and TS2 due to the formation of
intermolecular hydrogen bonds N–H···O and О–H···O
(2.472 and 1.907 Å respectively, Scheme 3).
It follows from the table that already at equimolar
ratio of reagents aminodiol 7 is formed in large enough
quantities (27–44%). Hence this aminolysis feature of
aryl glycidyl ethers is not connected with the amine
nature and, probably, has common character both for
sterically hindered amine 2 and highly reactive amine
(benzylamine). The polarity of the solvent has an
insignificant effect (yields of aminoalcohol 6 56–
73%). The presence of the a catalyst [Zn(ClO4)2–
Al2O3, Ca(OTf)2, Sulfated Zirconia, Mg(ClO4)2,
graphite oxide] significantly increases not only the
reaction rate, but also the yield of aminoalcohol 6 to
88% [20–26]. To reach this excess of aminoalcohol 6
(ratio to aminodiol 7 >20 : 1) in the absence of a
catalyst requires more than five-fold molar excess of
benzylamine with respect to initial epoxide 5 (see the
table).
Reactions of aminoalcohol 6 were described in
detail [27–31]. It forms N-acyl(alkyl)derivatives,
mesylates, sultames, 1,3-oxazolines, 2,5-disubstituted
morpholines, azetidines. The reactivity of aminodioles
of this type was far less understood. Considering the
method we developed of aminodiols preparation is
seems timely to develop a procedure of transforming
them into the corresponding morpholine derivatives,
whose medical application is doubtless [32]. More than
that, 2,6-disubstituted morpholines are used as active
ingredients in agrochemical compositions to treat the
cereal diseases [33].
By an example of benzyl derivative 7 we tested
various cyclization methods of aminodiols into mor-
pholine derivatives and found that intramolacular
cyclization of compound 7 in conditions of Mitsunobu
reaction gave morpholine derivative 8 in a good yield.
By reduction of the latter on palladium catalyst we
We made an attempt to understand the easy
generation of aminodiol [11] basing on the data of
quantum-chemical calculation of possible paths of
reaction of glycidyl ether 5 and amine 2. The lower
value of activation energy of the epoxide cycle
obtained 2,6-bis(phenoxymethyl)morpholine
9
Scheme 4.
Ph
OPh
OPh
Ph
OPh
1.2 equiv PPh3,
1.2 equiv DEAD
5% Pd/C, H2 (atm)
MeOH, 25oC, 4 h
N
HN
N
PhMe, 25oC, 12 h
O
O
OH
PhO
OH
PhO
PhO
9
7
8
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 5 2017

COMPOSITION AND REACTIVITY OF AMINOLYSIS PRODUCTS OF PHENYL GLYCIDYL
659
Scheme 5.
Ph
OPh
N
Ph
O_
OPh
Ph
OH
Ph
Ph
O
+
PhO
O
O
P
N
O
PPh3
_
N
O
N
O
OH
H
O
N
O
N
PhO
7
O
Ph
10
11
Ph
Ph
O
+
O
P
N
O
O
N
H
O
Ph
OPh
O
12
Ph
OPh
H
_
HN
N
O
N
N
O
O
Ph
Ph
O
_
P
,
O
PhO
Ph
Ph
O
O
+
PhO
P
H
8
Ph
OEt
N
Ph
EtO
N
H
O
13
Scheme 6.
7
NO2
NO2
4
5
3
2
1.2 equiv PPh3,
1.2 equiv DEAD
1
O
6
O
9
11
8
10
O2N
N
N
PhMe, 25oC, 24 h
O2N
O
9'
OH
10'
11'
O
OH
O
15
14
Scheme 7.
PhO
OPh
OPh
1 equiv TsNH2,
0.1 equiv Na2CO3,
0.1 equiv TEBA
O
2.1 equiv NaH,
1 equiv Tf2O
40% HBr_AcOH (30 equiv),
PhOH (3 equiv)
Ts
N
HN
Ts
N
OH
DME, 80oC,
6 h, 90%
DCM, 40oC,
6 h, 80%
60oC, 4 h, 75%
O
O
OPh
PhO
PhO
PhO
OH
5
9
(Scheme 4) that might be used as a valuable building
block in combinatorial synthesis.
reacts further with [1,2-bis(ethoxycarbonyl)hydrazinyl]-
triphenylphosphonium 12, transforming into inter-
mediate 13, which releases triphenylphophine oxide
and results in finall reaction product 8 (Scheme 5).
The possible mechanism of morpholine 8 formation
includes the reaction of zwitter-ion 10, product of of
DEAD reaction with triphenylphosphine, with
symmetrical aminodiol 7. The generated anion 11
Similary from aminodiol 14 [10] morpholine
derivative 15 was obtained with a bicyclic norbornene
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 5 2017

PAL’CHIKOV et al.
660
scaffold (Scheme 6) that did not impede the
cyclization.
Mass spectrum: m/z 408.2 [M + Н]+. Found, %: C
73.83; H 6.91; N 3.67. C25H29NO4. Calculated, %: C
73.69; H 7.17; N 3.44.
Alternative three-step procedure of morpholine 9
synthesis in 54% yield was described previously [34,
35] (Scheme 7). The method we developed is also
three-step, but gives a general yield of 74% and is
easier to realize for the reagents are more available, the
process does not require strictly anhydrous conditions
and labor-consuming workup of the products.
1-(Benzylamino)-3-phenoxypropan-2-ol (6).
Second fraction. Yield 50–90%, mp 70–72°C, Rf 0.08
(ethyl acetate–hexane, 1 : 1). Spectral parameters
correspond to published data [21, 22].
4-Benzyl-2,6-bis(phenoxymethyl)morpholine (8).
To a cooled to 0°С mixture of 0.41 g (1 mmol) of
aminodiol 7 and 0.31 g (1.2 mmol) of triphenylphos-
phine in 20 mL of toluene were added 0.21 g (1.2 mmol)
of diethyl diazene-1,2-dicarboxylate (DEAD) and the
mixture was stirred at room temperature till the end of
reaction according to TLC data. The reaction mixture
was washed with brine (20 mL), the organic layer was
separated, from aqueous layer reaction products were
extracted with ethyl acetate (2 × 20 mL). Combined
organic fractions were dried with sodium sulfate and
concentrated in a vacuum. The reaction product was
isolated by column chromatography on silica gel
(eluent ethyl acetate–hexane, 1 : 5 > 1 : 1). Yield
0.32 g (81%), mp 113–115°C, Rf 0.85 (ethyl acetate).
IR spectrum, ν, cm–1: 2980, 1720, 1520, 1452,
EXPERIMENTAL
IR spectra were registered on a spectrophotometer
Spectrum One Perkin Elmer from tablets with KBr.
1Н NMR spectra were measured on a spectrometer
Varian-VXR with working frequency 300 MHz
from solutions of compounds in deuterochloroform
using its residual signal at 7.26 ppm as internal
reference. LCMS analysis of reaction mixtures was
performed on chromato-mass-spectrometer Agilent
1100 Series equipped with diode matrix detector
Agilent LC/MSD of SL series, in a chemical ionization
mode under atmospheric pressure (APCI). The
monitoring of reaction progress and checking the
purity of obtained compounds was carried out by TLC
on Silufol-60F254 plates, eluent ethyl acetate or its
mixture with hexane, development with iodine vapor.
Elemental analysis was performed on a Carlo Erba
analyzer.
1
1378, 1245, 1090. Н NMR spectrum δ, ppm: 2.90
m (4Н, 2СН2N), 3.95 m (2H, NCН2Ph), 4.10–4.20
(6Н, 2СН2OPh + 2CНОН), 6.88–7.00 (6H, Harom),
7.25–7.31 (9H, Harom). Found, %: C 77.30; H 7.21; N
3.48. C25H27NO3. Calculated, %: C 77.09; H 6.99; N
3.60.
Aminolysis of phenylglycidyl ether (5). General
procedure. To a solution of 0.700 g (4.66 mmol) of
phenyl glycidyl ether 5 in 10 mL of the corresponding
solvent (see the table) at vigorous stirring was added in
one portion 0.500 g (4.66 mmol) of benzylamine
(reagents ratios see in the table). The reaction mixture
was stirred for 24 h at 25°С, solvent was removed in a
vacuum (10 mmHg, 60°С). The residue was analyzed
by LCMS method and when necessary was subjected
to preparative chromatographic separation on column
filled with silica gel (eluent ethyl acetate–hexane, 1 : 3→
1 : 1), two fractions were isolated.
2,6-Bis(phenoxymethyl)morpholine (9). To
solution of 0.19 g (0.5 mmol) of compound 8 in 20 mL
of methanol was added 0.05 g of 5% palladium on coal
and the hydrogenation with gaseous hydrogen at
atmospheric pressure was carried out at active stirring.
After 4 h the catalyst was filtered off, the filtrate was
evaporated in a vacuum. Yield of solid residue 0.14 g
(96%), mp 65–70°С, Rf 0.20 (ethyl acetate). 1Н
NMR spectrum, δ, ppm: 2.15 br.s (1Н, NH), 2.90 d.d
(2Н, СН2N, J 2.8, 12.0 Hz), 3.12 d.d (2Н, СН2N,
J 5.0, 12.0 Hz), 4.15–4.19 (6Н, 2СН2OPh + 2CНОН),
6.94–7.32 (10H, Harom). Physicochemical constants of
compound 9 were described previously [34, 35].
1,1'-(Benzylazanediyl)bis(3-phenoxypropan-2-ol)
(7). First fraction. Yield 40–95%, oily substance, Rf
0.58 (ethyl acetate–hexane, 1 : 1). IR spectrum, ν, cm–1:
3260, 1600, 1585, 1501, 1460, 1365, 1340, 1239,
1075, 1042. 1Н NMR spectrum, δ, ppm: 1.40 br.s (2H,
2ОН), 2.78–2.91 (4Н, 2СН2N), 3.88–2.96 (6H,
2CН2OPh + NСН2Ph), 4.12 m (2H, 2CНОН), 6.88 d
(4H, Harom), 6.97 t (2H, Harom), 7.26–7.35 (9H, Harom).
4-[(Bicyclo[2.2.1]hept-5-en-endo-2-yl)methyl]-2,6-
bis[(4-nitrophenoxy)methyl]morpholine (15) was
obtained similarly to compound 8 from 0.51 g
(1 mmol) of aminodiol 14 [10]. Yield 0.29 g (59%),
mp 158–160°C, Rf 0.70 (ethyl acetate). IR spectrum, ν,
cm–1: 2930, 1590, 1520, 1450, 1343, 1260, 1108, 727.
1Н NMR spectrum, δ, ppm: 0.61 m (1H, H3n), 1.23 d
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 5 2017

COMPOSITION AND REACTIVITY OF AMINOLYSIS PRODUCTS OF PHENYL GLYCIDYL
661
2
(1H, H7a, J7s,7a 7.5 Hz), 1.40 d (1H, H7s), 1.81 m (1H,
12. Pal’chikov, V.A., Svyatenko, L.K., Plakhotnii, I.N., and
Kas’yan, L.I., Russ. J. Org. Chem., 2013, vol. 49, p. 686.
doi 10.1134/S1070428013050084
13. Kas’yan, L.I., Golodaeva, E.A., Kas’yan, A.O.,
Isaev, A.K., and Bondarenko, Ya.S., Visn. Dnipropetr.
Univer. Khimiya, 2007, p. 48.
14. Kas’yan, L.I., Golodaeva, E.A., Nadtoka, M.I., and
Kas’yan, A.O., Visn. Dnepropetrovs. Univer. Khimiya,
2002, p. 41.
H3x), 2.25–2.36 (3H, H8А,B, H2), 2.53–2.80 (4H, 2H9,
2H9'), 2.83 (2H, H1,4), 4.05–4.15 (6H, H10,10', 2H11,11'),
5.90 d.d (1H, H6, J6,5 5.1, J6,1 3.0 Hz), 6.15 d.d
3
3
3
(1H, H5, J5,4 2.7 Hz), 6.96 d (4Harom, J 9.0 Hz), 8.18
d (4Harom, J 9.0 Hz). Found, %: C 62.81; H 5.75; N
8.70. C26H29N3O7. Calculated, %: C 63.02; H 5.90; N
8.48.
Authors express their gratitude for the financial
support to the Ministry of Education and Science of
Ukraine (grants 0116U001520 and 0116U007412), and
also to the Ministry of Education and Science of the
Russian Federation (contract no. 02.а03.21.0008).
15. Kas’yan, A.O., Golodaeva, E.A., Tsygankov, A.V., and
Kas’yan, L.I., Russ. J. Org. Chem., 2002, vol. 38,
p. 1606. doi 10.1023/A:1022553832553
16. Kas’yan, L.I., Batog, A.E., Kas’yan, A.O., Gaponova, P.G.,
Savel’eva, O.A., and Golodaeva, E.A., Vopr. Khim.
Khim. Tekhnol., 2000, p. 34.
17. Kas’yan, L.I., Kostenko, L.I., Golodaeva, E.A.,
Radchenko, N.D., Bondarenko, Ya.S., and
Prid’ma, S.A., Vopr. Khim. Khim. Tekhnol., 2008, p. 16.
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