Synthesis of aryloxyacetaldehydes and N-(aryloxyethyl)cyclohexanamine hydrochloroides

Article abstract of DOI:10.1134/S1070428010070109

Oxidation of 2-(aryloxymethyl)oxiranes with periodic acid gave a series of aryloxyacetaldehydes which reacted with cyclohexylamine in THF, and subsequent reduction of Schiff bases thus obtained with sodium tetrahydridoborate resulted in the formation of the corresponding secondary amines which were isolated and characterized as hydrochlorides.

Full text of DOI:10.1134/S1070428010070109

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2010, Vol. 46, No. 7, pp. 1017–1020. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © D.S. Shapenova, M.K. Belyatskii, L.P. Panicheva, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 7,
pp. 1019–1022.
Synthesis of Aryloxyacetaldehydes and N-(Aryloxyethyl)cyclo-
hexanamine Hydrochloroides
D. S. Shapenova, M. K. Belyatskii, and L. P. Panicheva
Tyumen’State University, ul. Semakova 10, Tyumen’, 625003 Russia
e-mail: dshapenova@yandex.ru
Received June 17, 2009
Abstract—Oxidation of 2-(aryloxymethyl)oxiranes with periodic acid gave a series of aryloxyacetaldehydes
which reacted with cyclohexylamine in THF, and subsequent reduction of Schiff bases thus obtained with
sodium tetrahydridoborate resulted in the formation of the corresponding secondary amines which were
isolated and characterized as hydrochlorides.
DOI: 10.1134/S1070428010070109
Aryloxyethanamines are known to exhibit biolog-
ical activity. In particular, compounds acting as local
anesthetics, adrenergic neuron blocking agents [1, 2],
and dopamine D2-receptor inhibitors [3] were found
among aryloxyethanamine derivatives. These com-
pounds are commonly synthesized by alkylation of
phenols with 2-halo amines [1, 4] or of amines with
2-aryloxyethyl halides [4]. Also, reductive amination
of aryloxyacetaldehydes with the use of sodium tetra-
hydridoborate [2, 3, 5] or hydrogen over Pd/C [6] was
reported. However, the yields are not high, and they
rarely exceed 50%. For example, Sakurai et al. [3]
described the reaction of substituted phenoxyacetalde-
hydes with primary and secondary amine hydrochlo-
rides in methanol in the presence of triethylamine,
followed by reduction with NaBH4, which afforded
11–31% of the corresponding 2-phenoxyethanamines.
2-phenoxyethanol [7], by alkylation of phenols with
bromoacetaldehyde acetals and subsequent hydrolysis
[2, 8], by ozonolysis of allyl phenyl ethers [9], and by
oxidation of glycerol monophenyl ether with lead
tetraacetate [10]. The most appropriate procedure
seems to be oxidation of 2-(aryloxymethyl)oxiranes
with periodic acid in aqueous medium or aqueous di-
oxane, which was proposed in [11] for the synthesis of
phenoxyacetaldehyde.
In the present article we report on the synthesis of
2-(aryloxymethyl)oxiranes and their oxidation with
periodic acid to obtain aryloxyacetaldehydes. The
latter were converted into the corresponding N-cyclo-
hexyl imines which were reduced to amines with
sodium tetrahydridoborate. N-(Aryloxyethyl)cyclohex-
anamines were isolated and characterized as hydro-
chlorides.
Aryloxyacetaldehydes necessary for the synthesis
of aryloxyethanamines according to [3] can also be
prepared in several ways: by catalytic oxidation of
By heating substituted phenols with excess
2-(chloromethyl)oxirane in aqueous sodium hydroxide
we obtained the corresponding 2-(aryloxymethyl)-
Scheme 1.
O
NaOH, H2O, 85°C
O
H5IO6, H2O, dioxane
ArO
CHO
+
ArH
Cl
OAr
Ia–If
IIa–IIf
(1) cyclo-C6H11NH2, THF
(2) NaBH4, AcOH
HCl, Et2O
·HCl
ArO
ArO
N
N
H
H
IIIa–IIIf
IVa–IVf
Ar = Ph (a), 2-MeC6H4 (b), 4-MeC6H4 (c), 4-MeOC6H4 (d), 4-O2NC6H4 (e), 1-naphthyl (f).
1017

SHAPENOVA et al.
1018
oxiranes Ia–If in 57–78% yields (Scheme 1). The op-
timal amount of sodium hydroxide was 1.5 equiv (with
respect to initial phenol); when the amount of alkali
was smaller, the reaction was accompanied by forma-
tion of 3-aryloxy-1-chloropropan-2-ols as by-products.
a mass-selective detector [TR-5MS SQC quartz capil-
lary column, 15 m×0.25 mm, film thickness 0.25 μm;
injector temperature 200°C; oven temperature pro-
gramming from 40°C (1 min) to 200°C at a rate of
30 deg/min; carrier gas helium, flow rate 1 ml/min;
interface temperature 200°C; quadrupole temperature
200°C; electron impact, 70 eV].
The oxidation of oxiranes Ia–If with periodic acid
in aqueous dioxane on heating gave aryloxyacetalde-
hydes IIa–IIf in 41–73% yield. The reactions were
complete in 30–40 min at optimal temperature. The
structure of aldehydes IIa–IIf was confirmed by the
1H NMR spectra which contained signals typical of
aldehyde protons at δ 9.69–9.80 ppm. Aromatic
protons resonated in the region δ 6.42–8.20 ppm, and
signals from the methylene protons appeared at δ 4.41–
4.69 ppm. Compounds IIb and IIc also displayed
signals from methyl protons at δ 2.23 and 2.20 ppm,
respectively, and the hydroxymethyl group in IId gave
a signal at δ 3.77 ppm.
Oxiranes Ia–If (general procedure). A solution of
0.2 mol of phenol in 45.6 g (0.5 mol) of 2-(chloro-
methyl)oxirane was heated to 82–85°C, a solution of
12.0 g (0.3 mol) of sodium hydroxide in 30 ml of
water was added dropwise over a period of 1 h under
vigorous stirring, and the mixture was stirred at that
temperature until complete conversion of the initial
phenol. The organic phase was separated from the hot
mixture, washed with hot water (40 ml) and a saturated
aqueous solution of sodium chloride until neutral
reaction, dried over Na2SO4, and filtered. Excess
2-(chloromethyl)oxirane was distilled off under re-
duced pressure (20–25 mm), and the residue was dis-
tilled in a vacuum (Ia–Ic, If) or recrystallized (Id, Ie).
According to the GC–MS data, aryloxyacetalde-
hydes IIa–IIf reacted with cyclohexanamine in THF to
form the corresponding Schiff bases in almost quanti-
tative yield (reaction time 12–18 h), and the subse-
quent reduction (without isolation) with sodium tetra-
hydridoborate in acetic acid afforded 68–75% of
amines IIIa–IIIf. The molecular ion peaks in the mass
spectra of IIIa–IIIf had low intensity, and the base
peak was that with m/z 112 [CH2=NHC6H11]+. Amines
IIIa–IIIf were isolated and characterized as hydro-
chlorides IVa–IVf. In the 1H NMR spectra of IVa–IVf
we observed a complex multiplet at δ 1.00–1.20 ppm
due to methylene protons in the cyclohexane ring.
Triplets at δ 2.50 and 4.26–4.48 ppm were assigned to
the N+CH2 and OCH2 groups, respectively, and the
N+CH and N+H2 protons resonated as broadened sin-
glets at δ 2.98–3.20 and 9.10–9.37 ppm, respectively.
2-(Phenoxymethyl)oxirane (Ia) was synthesized
from 18.8 g of phenol; reaction time 3 h. Yield 19.6 g
(65%), colorless liquid, bp 96–98°C (4 mm), nD20
1.5306; published data [12]: bp 92°C (1 mm), nD20
1.5318.
=
=
2-(2-Methylphenoxymethyl)oxirane (Ib) was syn-
thesized from 21.6 g of 2-methylphenol; reaction time
2.5 h. Yield 20.4 g (62%), colorless liquid, bp 99–
102°C (4 mm), nD20 = 1.5270; published data [13]:
bp 262–263°C.
2-(4-Methylphenoxymethyl)oxirane (Ic) was syn-
thesized from 21.6 g of 4-methylphenol; reaction time
3.5 h. Yield 25.5 g (78%), colorless liquid, bp 107–
109°C (5 mm), nD20 = 1.5260; published data [12]:
bp 98°C (2 mm), nD20 = 1.5272.
EXPERIMENTAL
2-(4-Methoxyphenoxymethyl)oxirane (Id) was
synthesized from 24.8 g of 4-methoxyphenol; reaction
time 3 h. Yield 25.9 g (78%), colorless rhombic crys-
tals, mp 47–49°C (from petroleum ether); published
data: [14]: mp 48–48.5°C.
1
The H NMR spectra were recorded from solutions
in CDCl3 (IIa–IIf) or DMSO-d6 (IIIa–IIIf) on
a Bruker DPX spectrometer operating at 400 MHz;
tetramethylsilane was used as internal reference. The
IR spectra were measured on an FSM-1201 spectrom-
eter with Fourier transform from films (liquids) or KBr
pellets (crystalline substances). Thin-layer chromatog-
raphy was performed on a Sorbfil plates (STKh-1A
silica gel, layer thickness 110 μm, polyethylene tere-
phthalate support, UV-254 indicator; eluent chloro-
form; development with iodine vapor or UV light).
Gas chromatographic–mass spectrometric analysis was
performed on a TRACE GC Ultra instrument with
2-(4-Nitrophenoxymethyl)oxirane (Ie) was ob-
tained from 27.8 g of 4-nitrophenol; reaction time 9 h.
Yield 24.6 g (63%), light yellow crystals, mp 67.5–
68.5°C (from i-PrOH); published data [12]: mp 64°C.
2-(Naphthalen-1-yloxymethyl)oxirane (If) was
obtained from 28.8 g of 1-naphthol; reaction time 11 h.
Yield 22.8 g (57%), light yellow oily substance,
bp 162–165°C (4 mm), nD20 = 1.6110; published data
[15]: bp 118–122°C (0.25 mm), nD24 = 1.6112.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 7 2010

SYNTHESIS OF ARYLOXYACETALDEHYDES
1019
Aldehydes IIa–IIf were synthesized according to
the procedure described in [11].
(4-Nitrophenoxy)acetaldehyde (IIe) was synthe-
sized from 9.75 g (0.05 mol) of compound Ie using
11.4 g (0.05 mol) of periodic acid in a mixture of
45 ml of water and 20 ml of dioxane at 50°C; reaction
time 35 min. Yield 3.7 g (41%), light yellow crystals,
bp 175–182°C (3 mm), mp 73–74°C. IR spectrum,
ν, cm–1: 2820, 2730 (C–H, aldehyde); 1750 (C=O).
1H NMR spectrum, δ, ppm: 4.67 s (2H, CH2), 6.91 d
(2H, Harom, J = 9.3 Hz), 8.14 d (2H, Harom, J = 9.3 Hz),
9.78 s (1H, CHO). Mass spectrum, m/z (Irel, %): 181
(60.8) [M]+, 152 (100), 122 (18.7), 106 (10.7). Found,
%: C 52.95; H 4.02; N 7.83. C8H7NO4. Calculated, %:
C 53.04; H 3.90; N 7.73. M 181.15.
Phenoxyacetaldehyde (IIa) was synthesized from
11.2 g (0.075 mol) of compound Ia using 17.1 g
(0.075 mol) of periodic acid in 65 ml of water at 50°C;
reaction time 45 min. Yield 6.5 g (64%), colorless oily
substance, bp 79–82°C (6 mm), nD20 = 1.5350; pub-
lished data [11]: bp 69–73°C (2 mm), nD20 = 1.5380. IR
spectrum, ν, cm–1: 2820, 2720 (C–H, aldehyde); 1740
1
(C=O). H NMR spectrum, δ, ppm: 4.41 s (2H, CH2),
6.76–7.21 m (5H, Harom), 9.69 s (1H, CHO). Mass
spectrum, m/z (Irel, %): 136 (39.1) [M]+, 107 (50.5), 94
(4.0), 77 (100), 65 (8.9), 51 (28.7).
(2-Methylphenoxy)acetaldehyde (IIb) was syn-
thesized from 9.0 g (0.055 mol) of compound Ib using
12.7 g (0.055 mol) of periodic acid in 50 ml of water at
50°C; reaction time 1.5 h. Yield 4.33 g (53%), yellow
oily substance, bp 80.5–84.5°C (2 mm), n2D0 = 1.5205.
IR spectrum, ν, cm–1: 2827, 2725 (C–H, aldehyde);
(Naphthalen-1-yloxy)acetaldehyde (IIf) was syn-
thesized from 7.0 g (0.035 mol) of compound If and
8.0 g (0.035 mol) of periodic acid in a mixture of
40 ml of water and 15 ml of dioxane at 55°C; reaction
time 1.5 h. Yield 2.81 g (43%), orange oily substance,
bp 150–156°C (3 mm), nD20 = 1.6205; published data
[16]: bp 120–125°C (0.04 mm). IR spectrum, ν, cm–1:
1
1735 (C=O). H NMR spectrum, δ, ppm: 2.30 s (3H,
1
o-CH3), 4.54 s (2H, CH2), 6.64–7.16 m (4H, Harom),
9.85 s (1H, CHO). Mass spectrum, m/z (Irel, %): 150
(90.6) [M]+, 121 (62.3), 108 (10.3), 107 (26.6), 91
(100), 77 (23.9), 65 (27.7). Found, %: C 71.72; H 6.66.
C9H10O2. Calculated, %: C 71.98; H 6.71. M 150.17.
2820, 2722 (C–H, aldehyde); 1735 (C=O). H NMR
spectrum, δ, ppm: 4.49 s (2H, CH2), 6.42–8.20 m
(7H, Harom), 9.76 s (1H, CHO). Mass spectrum, m/z
(Irel, %): 186 (100) [M]+, 157 (37.0), 143 (44.2), 127
(38.2), 115 (73.1).
(4-Methylphenoxy)acetaldehyde (IIc) was synthe-
sized from 8.2 g (0.05 mol) of compound Ic using
11.4 g (0.05 mol) of periodic acid in a mixture of
50 ml of water and 20 ml of dioxane at 55°C; reaction
time 40 min. Yield 3.95 g (53%), yellow oily substance,
bp 87–92°C (3 mm), nD20 = 1.5269. IR spectrum, ν,
cm–1: 2822, 2720 (C–H, aldehyde); 1740 (C=O).
1H NMR spectrum, δ, ppm: 2.20 s (3H, CH3), 4.41 s
(2H, CH2), 6.68–6.71 m (2H, Harom), 6.99–7.01 m (2H,
Harom), 9.72 s (1H, CHO). Mass spectrum, m/z (Irel, %):
150 (83.1) [M]+, 121 (92.6), 108 (7.6), 107 (8.5), 91
(100), 77 (28.2), 65 (24.1). Found, %: C 71.72; H 6.90.
C9H10O2. Calculated, %: C 71.98; H 6.71. M 150.17.
Amine hydrochlorides IVa–IVf (general proce-
dure). A solution of 6.1 mmol of aldehyde IIa–IIf in
20 ml of tetrahydrofuran was added under nitrogen to
a solution of 630 mg (6.4 mmol) of cyclohexanamine
in 5 ml of THF, and the mixture was stirred for 1 h at
room temperature and was then kept for 18 h at 4°C.
The mixture was cooled to 0°C, 180 mg (4.5 mmol) of
sodium tetrahydridoborate was added, the mixture was
stirred until gas evolution ceased, a solution of 180 mg
(3.0 mmol) of acetic acid in 5 ml of THF was added
dropwise over a period of 40 min, and the mixture was
stirred for 45 min. The mixture was treated with 25 ml
of a 10% aqueous solution of sodium hydroxide and
extracted with diethyl ether, the extract was dried over
MgSO4 and filtered, the filtrate was cooled to 0°C,
a solution of hydrogen chloride in diethyl ether was
added, and the precipitate was filtered off.
(4-Methoxyphenoxy)acetaldehyde (IId) was syn-
thesized from 8.5 g (0.047 mol) of compound Id using
17.1 g (0.05 mol) of periodic acid in a mixture of
50 ml of water and 20 ml of dioxane at 45°C; reaction
time 20 min. Yield 5.69 g (73%), yellow oily sub-
stance, bp 138–142°C (2 mm), nD20 = 1.5393. IR spec-
trum, ν, cm–1: 2835, 2715 (C–H, aldehyde); 1740
(C=O). 1H NMR spectrum, δ, ppm: 3.77 s (3H, CH3O),
4.52 s (2H, CH2), 6.84 s (4H, Harom), 9.84 s (1H,
CHO). Mass spectrum, m/z (Irel, %): 166 (96.2) [M]+,
137 (28.9), 108 (10.3), 123 (100), 107 (18.9), 95
(19.7), 77 (37.3). Found, %: C 64.65; H 6.14. C9H10O3.
Calculated, %: C 65.05; H 6.07. M 166.17.
N-(2-Phenoxyethyl)cyclohexanamine hydro-
chloride (IVa). Yield 1.11 g (71%), colorless needles,
1
mp 168–170°C. H NMR spectrum, δ, ppm: 1.01–
2.12 m (10H, (CH2), 2.50 t (2H, N+CH2, J = 1.8 Hz),
2.99–3.08 br.s (1H, N+CH), 4.29 t (2H, OCH2, J =
5.2 Hz), 6.96–7.34 m (5H, Harom), 9.10–9.21 br.s (2H,
N+N2). Mass spectrum of free amine IIIa, m/z (Irel, %):
219 (5.9) [M]+, 176 (11.9), 112 (100). Found, %:
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 7 2010

SHAPENOVA et al.
1020
C 65.51; H 8.42; N 5.56. C14H21NO·HCl. Calculated,
%: C 65.74; H 8.67; N 5.48. M 219.32.
spectrum, δ, ppm: 1.06–2.20 m (10H, CH2), 2.50 t (2H,
N+CH2), 3.07–3.18 br.s (1H, N+CH), 4.48 t (2H,
OCH2, J = 5.0 Hz), 6.99 d (1H, 2-H, J = 7.5 Hz),
7.44 d (1H, 4-H, J = 7.8 Hz), 7.50–7.57 m (3H, 3-H,
6-H, 7-H), 7.88 d (1H, 5-H, J = 6.8 Hz), 8.37 d (1H,
8-H, J = 7.5 Hz), 9.30– 9.37 br.s (2H, N+H2). Mass
spectrum of free base IVf, m/z (Irel, %): 269 (16.1)
[M]+, 226 (7.0), 126 (66.4), 112 (100). Found, %:
C 70.55; H 8.09; N 4.62. C18H23NO·HCl. Calculated,
%: C 70.69; H 7.91; N 4.58. M 269.38.
N-[2-(2-Methylphenoxy)ethyl]cyclohexanamine
hydrochloride (IVb). Yield 1.02 g (62%), colorless
1
crystals, mp 160–162°C. H NMR spectrum, δ, ppm:
1.07–2.15 m (10H, CH2), 2.22 s (3H, CH3), 2.50 t (2H,
N+CH2, J = 1.9 Hz), 3.06–3.14 br.s (1H, N+CH), 4.30 t
(2H, OCH2, J = 5.3 Hz), 6.86–7.18 m (4H, Harom),
9.13–9.24 br.s (2H, N+H2). Mass spectrum of free
amine IIIb, m/z (Irel, %): 233 (23.8) [M]+, 190 (15.8),
112 (100). Found, %: C 66.88; H 8.85; N 5.08.
C15H23NO·HCl. Calculated, %: C 66.77; H 8.97;
N 5.19. M 233.35.
REFERENCES
1. Roe, A.M., Burton, R.A., Willey, G.L., Baines, M.W.,
and Rasmussen, A.C., J. Med. Chem., 1968, vol. 11,
p. 814.
N-[2-(4-Methylphenoxy)ethyl]cyclohexanamine
hydrochloride (IVc). Yield 1.21 g (74%), white crys-
tals, mp 159–160°C. 1H NMR spectrum, δ, ppm: 1.06–
2.11 m (10H, CH2), 2.24 s (3H, CH3), 2.50 t (2H,
N+CH2, J = 1.8 Hz), 2.95–3.06 br.s (1H, N+CH), 4.27 t
(2H, OCH2, J = 5.4 Hz), 6.88 d (2H, Harom, J = 8.6 Hz),
7.12 d (2H, Harom, J = 8.2 Hz), 9.27–9.36 br.s (2H,
N+H2). Mass spectrum of free amine IIIc, m/z (Irel, %):
233 (12.8) [M]+, 190 (12.8), 112 (100). Found, %:
C 66.51; H 8.82; N 5.09. C15H23NO·HCl. Calculated,
%: C 66.77; H 8.97; N 5.19. M 233.35.
2. Nelson, W.L. and Powell, M.L., J. Med. Chem., 1979,
vol. 22, p. 1125.
3. Sakurai, S., Mitani, K., Hashimoto, S., Morikawa, K.,
Yasuda, S., Koshinaka, E., Kato, H., and Ito, Y., Chem.
Pharm. Bull., 1992, vol. 40, p. 1443.
4. Sandberg, R., Russian Patent no. 2193555, 2002;
http://ru.espacenet.com.
5. Rosini, M., Antonello, A., Cavalli, A., Bolognesi, M.L.,
Minarini, A., Marucci, G., Poggesi, E., Leonardi, A., and
Melchiorre, C., J. Med. Chem., 2003, vol. 46, p. 4895.
6. Acetti, D., Brenna, E., and Fuganti, C., Tetrahedron:
Asymmetry, 2007, vol. 18, p. 488.
7. Shostakovskii, M.F., Keiko, N.A., Chichkarev, A.P., and
Keiko, V.V., USSR Inventor’s Certificate no. 290902,
1970; Byull. Izobret., 1971, no. 3.
N-[2-(4-Methoxyphenoxy)ethyl]cyclohexan-
amine hydrochloride (IVd). Yield 1.17 g (67%).
1
colorless crystals, mp 140–142°C. H NMR spectrum,
δ, ppm: 1.08–2.11 m (10H, CH2), 2.51 t (2H, N+CH2,
J = 1.9 Hz), 2.98–3.06 br.s (1H, N+CH), 3.71 s (3H,
OCH3), 4.25 t (2H, OCH2, J = 5.3 Hz), 6.87–6.95 m
(4H, Harom), 9.20–9.32 br.s (2H, N+H2). Mass spectrum
of free amine IIId, m/z (Irel, %): 249 (10.1) [M]+, 206
(8.2), 126 (67.0), 112 (100). Found, %: C 62.34;
H 8.32; N 5.08. C15H23NO2·HCl. Calculated, %:
C 63.04; H 8.46; N 4.90. M 249.35.
8. Baganz, H. and Brinekmann, E., Chem. Ber., 1953,
vol. 86, p. 1318.
9. Jellen, W., Mittelbach, M., and Junek, H., Monatsh.
Chem., 1996, vol. 127, p. 167.
10. Hutch, L.F., J. Am. Chem. Soc., 1945, vol. 67, p. 39;
Speer, R.J. and Mahler, R.H., J. Am. Chem. Soc., 1949,
vol. 71, p. 1133.
N-[2-(4-Nitrophenoxy)ethyl]cyclohexanamine
hydrochloride (IVe). Yield 1.36 g (74%), light yellow
crystals, mp 205.5–207°C. 1H NMR spectrum, δ, ppm:
1.05–2.13 m (10H, CH2), 2.50 t (2H, N+CH2, J =
1.7 Hz), 3.00–3.11 br.s (1H, N+CH), 4.47 t (2H, OCH2,
J = 5.1 Hz), 7.20 d (2H, Harom, J = 9.1 Hz), 8.24 d
(2Harom, J = 9.3 Hz), 9.26–9.39 br.s (2H, N+H2). Mass
spectrum of free amine IIIe, m/z (Irel, %): 264 (1.7)
[M]+, 221 (24.8), 112 (100). Found, %: C 55.72;
H 7.21; N 9.09. C14H20N2O3·HCl. Calculated, %:
C 55.90; H 7.04; N 9.31. M 264.32.
11. Andreev, L.K., Derkach, L.G., and Kheifits, L.A.,
Zh. Org. Khim., 1978, vol. 14, p. 1285.
12. Klebanov, M.S., Kir’yazev, F.Yu., Chervinskii, A.Yu.,
and Shologon, I.M., Zh. Org. Khim., 1984, vol. 20,
p. 2407.
13. Khadikar, B.M. and Bendale, P.M., Synth. Commun.,
1997, vol. 27, p. 2051.
14. Ronda, J.C., Serra, A., and Cadiz, V., Macromol. Chem.
Phys., 1997, vol. 198, p. 2917.
15. Rauls, D.O. and Baker, J.K., J. Med. Chem., 1979,
vol. 22, p. 81.
N-[2-(Naphthalen-1-yloxy)ethyl]cyclohexan-
amine hydrochloride (IVf). Yield 1.31 g (70%),
colorless crystals, mp 237–238°C (decomp.). H NMR
16. Noe, C.R., Knollmueller, M., Gaertner, P., Fleisch-
hacker, W., and Katikarides, E., Monatsh. Chem., 1995,
vol. 126, p. 481.
1
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 7 2010