Synthesis of new cationics, carboxybetaines, and sulfobetaines bolaamphiphiles

Article abstract of DOI:10.1081/SCC-100000173

A new family of bolaform compounds with carboxybetaine or sulfobetaine heads was synthesized in excellent yield from a common intermediate: α,w-bis-(N,N-dimethylamino)-alkane. Dicationic bolaforms bearing esters groups also were isolated.

Full text of DOI:10.1081/SCC-100000173

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SYNTHESIS OF NEW CATIONICS, CARBOXYBETAINES,
AND SULFOBETAINES BOLAAMPHIPHILES
a
b
Souad Souirti & Michel Baboulè
a
Université Ibn Tofail , Laboratoire de Synthèse Organique et Réactivité, BP 133,
Kenitra, Maroc, 14000
b
Université Paul Sabatier , Laboratoire des Interactions Moléculaires et Réactivités
Chimique et Photochimique (CNRS, UMR 5623), 118 route de Narbonne, Toulouse Cédex,
31062, France
Published online: 09 Nov 2006.
To cite this article: Souad Souirti & Michel Baboulè (2001) SYNTHESIS OF NEW CATIONICS, CARBOXYBETAINES, AND
SULFOBETAINES BOLAAMPHIPHILES, Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 31:1, 9-18, DOI: 10.1081/SCC-100000173
To link to this article: http://dx.doi.org/10.1081/SCC-100000173
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SYNTHETIC COMMUNICATIONS, 31(1), 9–18 (2001)
SYNTHESIS OF NEW CATIONICS,
CARBOXYBETAINES, AND
SULFOBETAINES BOLAAMPHIPHILES
1
2,∗
Souad Souirti and Michel Baboul e` ne
1Laboratoire de Synth e` se Organique et R e´ activit e´ ,
Universit e´ Ibn Tofail, BP 133, 14000 K e´ nitra, Maroc
Laboratoire des Interactions Mol e´ culaires et R e´ activit e´ s
Chimique et Photochimique (CNRS, UMR 5623),
Universit e´ Paul Sabatier, 118 route de Narbonne,
2
31062 Toulouse C e´ dex, France
ABSTRACT
A new family of bolaform compounds with carboxybetaine
or sulfobetaine heads was synthesized in excellent yield from a
common intermediate: α,ω-bis-(N,N-dimethylamino)-alkane. Di-
cationic bolaforms bearing esters groups also were isolated.
There has been considerable interest in recent years in the synthesis and
physico-chemical properties of bolaamphiphile compounds (1). This class of sur-
factants, characterized by the presence of two hydrophilic heads linked by a long
hydrophobic chain, can now be prepared by “modular” synthesis. These com-
pounds are of value for construction of model biological membranes and have
applications in pharmacology (2–4) and chemical catalysis (5,6).
∗
To whom correspondence should be addressed. Fax: +33 5 61 25 17 33; E-mail: mbab@
ramses.ups-tlse.fr
9
Copyright ꢀC 2001 by Marcel Dekker, Inc.
www.dekker.com

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1
0
SOUIRTI AND BABOULENE
The diionic bolaforms (anionic and/or cationic) have been the first to ex-
hibit self-association and now have industrial applications (7–10). These novel
compounds have also been prepared with sugar (11) and non-ionic heads (12).
To our knowledge there are no reports on betaine bolaforms, although
monozwitterionic amphiphiles have formed the subject of numerous studies and
applications (13–15). Despite the presence of an electrically charged polar head,
these surfactants are electrically neutral, which makes them compatible with bi-
ological systems and confers applications in biochemistry and cosmetology. As
betaine bolaforms have interest from synthetic, fundamental and applied points of
view, we describe here the synthesis of novel bolaforms 1 and 2 with carboxybe-
taine or sulfobetaine heads.
SYNTHESIS
Results and Discussion
Route to Carboxybetaine Bolaforms 1
By analogy with previous methods of synthesis of monobetaine amphiphiles,
two routes were selected. The first was a direct condensation of a long chain
dihaloalkane with dimethyl glycine (Scheme 1).
After a number of attempts using different reaction conditions, we failed to
obtain complete diquarternization of the nitrogen atoms. Various by-products were
formed, hindering recovery of the major compounds 3. It should be noted that the
compounds 3 had a correct elemental analysis, provided they were associated with
two equivalents of sodium bromide. Our attempts at separation were unsuccessful;
the stoichiometry of compound 3: NaBr was consistent at 1:2.
On the other hand, excellent yields of the novel bicatenary cationic bolaforms
4
were obtained (Scheme 1) by heating with an excess of the dihalogenated deriva-
tives. Their properties are currently under investigation.
To avoid these difficulties, a two-stage process was studied starting from
dimethylamine via α,ω bis-(N,N-dimethylamino) alkane 5 (Scheme 2).
We obtained an almost quantitative quaternization of the two nitrogen atoms
of the diamine 5 by bromoacetic acid in basic medium. The compounds isolated
were identical to the compounds 3 prepared by the first method described above.

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BOLAFORM COMPOUNDS
11
Scheme 1. Synthetic Route to Compounds 3.
Scheme 2. Synthetic Route to Compounds 1, 3, 6, and 7.
For synthesis of amphiphilic monocarboxybetaines, the presence of a sodium salt
in various stoichiometries ranging from 1 to 2.5 equivalents/mole has been reported
as a difficulty (16–21). A reaction in neutral medium can be obtained by the use of
ethyl bromoacetate as alkylating agent. In ether in the cold, diquaternization was
total for one hour reaction. By to warm to reflux, we observed a transesterification
process. The novel dicationic bolaforms 6 and 7 were readily isolated in good yield
(
Table 1).

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`
1
2
SOUIRTI AND BABOULENE
Table 1. Yields and Melting Points for Compounds Prepared
Products
n
1a
8
1b
12
2a
8
2b
12
3a
8
3b
12
6a
8
6b
12
7a
8
7b
12
yield (%)
mp ( C)
95
260
92
180
95
210
95
215
94
220
88
170
98
180
98
140
98
197
98
145
◦
Theywereemployedasintermediatestoaffordthecarboxybetainebolaforms
in quantitative yield. Simple reaction in alcoholic medium in the presence of a
1
strongly basic ion exchange resin produced the carboxybetaine structure directly
(
(
20) devoid of sodium salt. Table 1 lists details of the two series of bolaforms
n = 8 or 12) prepared by this method.
Route to the Sulfobetaine Bolaforms 2
We employed a procedure based on that of Fendler et al. (22) for the syn-
thesis of amphiphilic monosulfobetaines. The diamine 5 prepared as described
above was the main reactant (Scheme 3). The disulfobetaines 2 were obtained
in quantitative yield on heating the reaction mixture (Table 1). However, we
noted that in the cold and even with excess sultone, only the monosulfobetaine
was obtained in quantitative yield. The disulfobetaine 2 was obtained by heat-
ing the mixture with a further equivalent of sultone. Apart from their interest
as surfactants, these compounds offer a convenient route to novel disymmet-
ric bolaforms, which are under investigation in our laboratory. The recent re-
ꢁ
port of Spencer et al. (23) on the synthesis of N,N -bis(trimethylammonium-
1)-4-butylsulfonyl dodecane (yield around 18%), which has inhibitory activity
towards squalene synthetase, indicates the potential biological applications of
betaine bolaforms.
Scheme 3. Synthetic Route to Compounds 2.

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BOLAFORM COMPOUNDS
13
CONCLUSION
We describe here the synthesis of novel betaine bolaform derivatives. Series
of carboxybetaine, sulfobetaine, and cationic bolaforms were prepared in excellent
yield using the synthon α,ω-bis-(N,N-dimethylamino) alkane. The process is easy
and could be scaled up for industrial applications. The method permits access to
a wide range of bolaform derivatives, opening new fields of investigation of both
fundamental and applied interest.
EXPERIMENTAL
General
Commercial quality reagents were used without purification. Melting points
−
1
(
uncorrected) were obtained on a Kofler Prolabo apparatus. IR spectra (ν, cm )
1
13
were recorded on a Perkin-Elmer 683 spectrophotometer. H and C NMR spectra
δ, ppm, TMS as internal reference) were obtained on Bruker AC 80 or Bruker AC
00 instruments.
(
2
Typical Procedure for the Synthesis of Compounds 5
−
−2
2
A solution of dimethylamine (33% of ethanol) (3 10 mol) and dibro-
−2
moalkane (10 mol) was added to sodium carbonate (2 10 mol) in 60 ml of
ethanol and 15 ml of water. The reaction mixture was stirred at reflux for 24 h.
Then the resulting compound was isolated by filtration and evaporating of the
solvent under reduced pressure. The crude product, washed with 10 ml of water,
was extracted with EtO2. The organic phase was dried on anhydrous Na2SO4 and
evaporated in vacuo. The crude oil was purified by distillation.
1,8-bis(N,N-dimethylamino)octane, 5a
◦
1
Yield: 98%. Colourless oil, bp = 40 C/0.02 Torr. H NMR (200 MHz,
1
3
CDCl3): δ 1.1 (m, 12H, (CH2)6), 1.9 (m, 16H, NCH2, NCH3); C NMR (200 MHz,
CDCl3): δ 27.23–28.3 ((CH2)6), 45.20 (NCH3), 59.66 (NCH2). Anal calcd. (%)
for C12H28N2 (200.37), C: 71.93; H: 14.09; N: 13.97; found, C: 71.66; H: 14.15;
N: 14.13.
1,12-bis(N,N-dimethylamino)dodecane, 5b
◦
1
Yield: 98%. Colourless oil, bp = 80–82 C/0.05 Torr. H NMR (200 MHz,
1
3
CDCl3): δ 1.1 (m, 20H, (CH2)10), 2.05 (m, 16H, NCH2, NCH3); C NMR

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`
1
4
SOUIRTI AND BABOULENE
(
200 MHz, CDCl3): δ 27.43–28.53 ((CH2)10), 45.42 (NCH3), 59.87 (NCH2). Anal
calcd. (%) for C16H36N2 (256.47), C: 74.86; H: 14.03; N: 10.92; found, C: 74.73;
H: 13.90; N: 10.62.
Typical Procedure for the Synthesis of Compounds 3
−
2
Bromoacetic acid (2.2 10 mol) was added to a mixture of α,ω-bis(N,N-
−2
−2
dimethylamino)-alkane 5 (10 mol) in MeOH (50 ml) and Na2CO3 (2 10 mol).
The reaction mixture was stirred at reflux for 24 h. The mineral compounds
were separated by filtration. The solvent was evaporated in vacuo. The white
product was collected, washed successively with acetone and ether, and dried in
vacuo.
1,8-bis(N,N-dimethyl, N-sodium acetate ammonium bromide)octane, 3a
◦
+
Yield: 94%. White powder, mp = 220 C. IR (KBr): ν 1480 (C–N ), 1750
−
1
(
1
C == O), 1610 (CO ). H NMR (80 MHz, D2O): δ 1.2 (m, 12H, (CH2)6), 3.1 (m,
2H, NCH3), 3.4 (t, 4H, NCH2), 3.7 (s, 4H, CH2CO2); C NMR (200 MHz, D2O):
2
1
3
δ 24.53–30.34 (6C, (CH2)6), 53.81 (NCH3), 66.14 (NCH2), 67.21 (CH2CO2),
1
6
71.95 (CO2). Anal calcd. (%) for C16H32N2O4Na2Br2 (522.23), C: 36.78; H:
.13; N: 5.36; found, C: 36.20; H: 6.61; N: 4.99.
1,12-bis(N,N-dimethyl, N-sodium acetate ammonium bromide)dodecane, 3b
◦
+
Yield: 88%. White powder, mp = 170 C. IR (KBr): ν 1480 (C–N ), 1750
−
1
(
C == O), 1610 (CO ). H NMR (200 MHz, D2O): δ 1.2 (m, 16H, (CH2)8), 1.6 (m,
2
4
H, N–C–CH2), 3.14 (m, 12H, NCH3), 3.4 (t, 4H, NCH2), 3.7 (s, 4H, CH2CO2);
C NMR (200 MHz, D2O): δ 24.5–31 ((CH2)10), 53.6 (NCH3), 66 (NCH2), 67.2
CH2CO2), 171.8 (CO2). Anal calcd. (%) for C20H40N2O4Na2Br2 (578.34), C:
1
3
(
41.52; H: 6.92; N: 4.84; found, C: 41.13; H: 7.09; N: 4.81.
Typical Procedure for the Synthesis of Compounds 7 and 6
−
2
−2
A mixture of diamine 5 (10 mol) and ethyl bromoacetate (2.3 10 mol)
in ether (40 ml) was stirred for 1 h at room temperature (route a), or in alcohol
heated at reflux under agitation for 6 h (route b). The solvent was evaporated in

ORDER
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BOLAFORM COMPOUNDS
15
vacuo. The residual oil was triturated from ether. The crude solid was purified by
crystallisation from methanol-ether: (1–9).
1,8-bis(N,N-dimethyl, N-ethyl acetate ammonium bromide)octane, 7a
◦
Yield: 98%. White powder, mp = 196–198 C. IR (KBr): ν 1500–1400
+
1
(
C–N ), 1750 (C == O), 1250 (CO2Et). HNMR (80 MHz, D2O): δ 1.2 (m, 18H,
CH2)6, CH3-C), 3.2 (m, 16H, NCH2, NCH3), 4.3 (m, 8H, CH2-CH3, CH2CO );
C NMR (200 MHz, D2O): δ 15.7 (CH3-C), 24–30 ((CH2)6), 54 (NCH3), 63.8
−
(
2
1
3
(
NCH2), 66 (OCH2), 68.3 (CH2CO2), 167.8 (CO2). Anal calcd. (%) for C20H42N2
O4Br2 (534.37), C: 44.95; H: 7.92; N: 5.24; found, C: 44.36; H: 7.94;
N: 5.09.
1,12-bis(N,N-dimethyl, N-ethyl acetate ammonium bromide)dodecane, 7b
◦
+
Yield: 98%. White powder, mp = 145 C. IR (KBr): ν 1500–1400 (C–N ),
1
1
750 (C == O), 1235 (CO2Et). H NMR (80 MHz, D2O): δ 1.2 (m, 26H, (CH2)10,
CH3-C), 3.2 (m, 16H, NCH2, NCH3), 4.3 (m, 8H, CH2-CH3, CH2CO );
−
13
C
2
NMR (200 MHz, D2O): δ 15.9 (CH3-C), 24.7–31.37 ((CH2)10), 54.60 (NCH3),
3.8 (NCH2), 66 (OCH2), 68.2 (CH2CO2), 167.8 (CO2). Anal calcd. (%) for
6
C24H50N2O4Br2 (590.48), C: 48.77; H: 8.46; N: 4.75; found, C: 48.98; H: 8.12;
N: 4.53.
1,8-bis(N,N-dimethyl, N-methyl acetate ammonium bromide)octane, 6a
◦
+
Yield: 98%. White powder, mp = 180 C. IR (KBr): ν 1500–1400 (C–N ),
1
1
1
750 (C == O), 1240 (CO2CH3). H NMR (200 MHz, D2O): δ 1.3 (m, 8H, (CH2)4),
.7 (qt, 4H, N–C–CH2), 3.2 (m, 12H, NCH3), 3.5 (t, 4H, NCH2), 3.6 (s, 6H,
1
3
OCH3), 4.2 (s, 4H, CH2CO2); C NMR (200 MHz, D2O): δ 24.5–30.3 ((CH2)6),
4.2 (NCH3), 55.9 (OCH3), 63.7 (NCH2), 66.4 (CH2CO2), 68.2 (CH2CO2), 168.3
CO2). Anal calcd. (%) for C18H38N2O4Br2 (506.32), C: 42.7; H: 7.56; N: 5.53;
found, C: 42.59; H: 7.86; N: 4.98.
5
(
1,12-bis(N,N-dimethyl, N-methyl acetate ammonium bromide)dodecane, 6b
◦
+
Yield: 98%. White powder, mp = 140 C. IR (KBr): ν 1500–1400 (C–N ),
1
1
750 (C == O), 1255 (CO2CH3). H NMR (200 MHz, D2O): δ 1.2 (m, 16H, (CH2)8),

ORDER
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`
SOUIRTI AND BABOULENE
1
6
1
4
.7 (qt, 4H, N–C–CH2), 3.1 (m, 12H, NCH3), 3.4 (t, 4H, NCH2), 3.7 (s, 6H, OCH3),
.2 (s, 4H, CH2CO2); 13C NMR (200 MHz, D2O): δ 24.4–31.1 ((CH2)10), 54.2
(
(
NCH3), 55.8 (OCH3), 63.6 (NCH2), 68.4 (CH2CO2), 168.3 (CO2). Anal calcd.
%) for C22H46N2O4Br2 (562.43), C: 46.98; H: 8.42; N: 4.98; found, C: 46.34;
H: 8.09; N: 4.72.
Typical Procedure for the Synthesis of Compounds 1
−
2
A mixture of compound 6 or 7 (10 mol) and 25 g of anion-exchange resin
−
(
OH ) (IRA 400) was stirred for 3 h at room temperature. Then the mixture was
filtered and evaporated in vacuo. The residual oil was triturated from ether and
crystallised from ether-methanol: (9–1).
1,8-bis(N,N-dimethyl, carboxybetaine)octane, 1a
◦
+
Yield: 95%. White powder, mp = 260 C. IR (KBr): ν 1480 (C-N ), 1750
1
(
(
C == O), 1610 (CO2). H NMR (80 MHz, D2O): δ 1.26 (m, 12H, (CH2)6), 3.09
m, 12H, NCH3), 3.4 (t, 4H, NCH2), 3.7 (s, 4H, CH2CO2); C NMR (200 MHz,
1
3
D2O): δ 24.51–30.33 ((CH2)6), 53.8 (NCH3), 66.14 (NCH2), 67.14 (CH2CO2),
1
8
71.82 (CO2). Anal calcd. (%) for C16H32N2O4 (316.44), C: 60.73; H: 10.19; N:
.85; found, C: 60.90; H: 10.22; N: 8.63.
1,12-bis(N,N-dimethyl, carboxybetaine)dodecane, 1b
◦
+
Yield: 92%. White powder, mp = 180 C. IR (KBr): ν 1480 (C–N ), 1750
1
(
(
C == O), 1610 (CO2). H NMR (80 MHz, D2O): δ 1.19 (m, 20H, (CH2)10), 3.06
m, 12H, NCH3), 3.4 (t, 4H, NCH2), 3.7 (s, 4H, CH2CO2); C NMR (200 MHz,
1
3
D2O): δ 24.57–31 ((CH2)10), 53.7 (NCH3), 66.12 (NCH2), 67.25 (CH2CO2), 171.8
CO2). Anal calcd. (%) for C20H40N2O4 (372.55), C: 64.48; H: 10.82; N: 7.52;
found, C: 63.97; H: 10.94; N: 6.97.
(
Typical Procedure for the Synthesis of Compounds 2
−
2
Compounds 2 were prepared by the addition of diamine 5 (10 mol) to
−2
1
.3 propane sultone (2.2 10 mol) in 100 ml of anhydrous acetonitrile. The
solution was stirred at reflux for 4 h, then cooled and filtered. After crystallisation
from methanol-acetone (1–9), pure compounds 2 were obtained as solid which
decomposed during melting point determination.

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BOLAFORM COMPOUNDS
17
1,8-bis(N,N-dimethyl, 1–3 propanesulfobetaine)octane, 2a
◦
+
Yield: 95%. White powder, mp = 210 C. IR (KBr): ν 1480 (C-N ), 1040
1
(
S == O). H NMR (200 MHz, D2O): δ 1.2 (m, 12H, (CH2)6), 1.9 (qt, 4H, CH2-C-
SO3), 2.9 (t, 4H, CH2SO3), 3.02 (s, 12H, NCH3), 3.24 (t, 4H, CH2N), 3.38 (t, 4H,
CH2N); 13C NMR (200 MHz, D2O): δ 20.69–31.06 ((CH2)6), 49.82 (CH2-C-SO3),
5
3.12 (NCH3), 64.4 (NCH2), 66.7 (CH2SO3). Anal calcd. (%) for C18H40N2S2O6
444.64), C: 48.62; H: 9.07; N: 6.30, S: 14.42; found, C: 48.96; H: 9.30; N: 5.94;
S: 13.97.
(
1,12-bis(N,N-dimethyl, 1–3 propanesulfobetaine)dodecane, 2b
◦
+
Yield: 95%. White powder, mp = 215 C. IR (KBr): ν 1480 (C-N ), 1040
1
(
S == O). H NMR (200 MHz, D2O): δ 1.2 (m, 20H, (CH2)10), 2.2 (qt, 4H, CH2-C-
SO3), 2.6 (t, 4H, CH2SO3), 3.03 (s, 12H, NCH3), 3.18 (t, 4H, CH2N), 3.3 (t, 4H,
CH2N); 13C NMR (200 MHz, D2O): δ 20.7–31.09 ((CH2)10), 49.8 (CH2-C-SO3),
5
3.14 (NCH3), 64.4 (NCH2), 66.8 (CH2SO3). Anal calcd. (%) for C22H48N2S2O6
500.75), C: 52.77; H: 9.66; N: 5.29, S: 12.8; found, C: 52.13; H: 9.42; N: 5.39;
S: 12.23.
(
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