(S)-2-(Aminomethyl)-1-ethylpyrrolidine supplier

Name
(S)-2-(Aminomethyl)-1-ethylpyrrolidine
EINECS 607-160-6
CAS No. 22795-99-9
Article Data6
CAS DataBase
Density 0.902 g/cm³
Solubility Soluble in chloroform, methanol. Slightly soluble in water.
Melting Point
Formula C₇H₁₆N₂
Boiling Point 161.9 °C at 760 mmHg
Molecular Weight 128.217
Flash Point 60.6 °C
Transport Information UN 1993 3/PG 3
Appearance Clear colorless to faintly yellow liquid
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Pyrrolidinemethanamine,1-ethyl-, (S)-;Pyrrolidine, 2-(aminomethyl)-1-ethyl-, (-)- (8CI);(-)-(S)-2-(Aminomethyl)-1-ethylpyrrolidine;(-)-2-(Aminomethyl)-1-ethylpyrrolidine;(S)-(-)-1-Ethyl-2-pyrrolidinemethanamine;(S)-(1-Ethylpyrrolidin-2-yl)methanamine;S-(-)-2-(Aminomethyl)-N-ethylpyrrolidine;[[(2S)-1-Ethylpyrrolidin-2-yl]methyl]amine;S-(-)N-ethyl-2-aminomethylpyrrolidine;
PSA 29.26000
LogP 1.06760

Synthetic route

: 66158-71-2
(S)-1-acetyl-2-(azidomethyl)pyrrolidine

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 8h;	75%

: 114812-34-9
(-)-(S)-1-ethyl-2-pyrrolidinecarboxamide

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;	69%
With lithium aluminium tetrahydride In tetrahydrofuran Inert atmosphere;
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 19.5h; Inert atmosphere; Reflux;

: 938-54-5
1-ethyl-pyrrolidine-2-carboxylic acid ethyl ester

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / liquid NH3, molecular sieves 3A / methanol / 20 h / 50 °C 2: 69 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme

: 147-85-3
L-proline

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / K2CO3 / dimethylformamide / 3 h / Ambient temperature 2: 88 percent / liquid NH3, molecular sieves 3A / methanol / 20 h / 50 °C 3: 69 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme

: 66158-68-7
(S)-1-(2-(hydroxymethyl) pyrrolidin-1-yl)ethanone

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 79 percent / SOCl2 / CHCl3 / 4.5 h / 0 °C 2: 87 percent / NaN3, KI / dimethylformamide / 8 h 3: 75 percent / LiAlH4 / diethyl ether / 8 h View Scheme

: 66158-70-1
(S)-1-acetyl-2-(chloromethyl)pyrrolidine

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / NaN3, KI / dimethylformamide / 8 h 2: 75 percent / LiAlH4 / diethyl ether / 8 h View Scheme

: 23356-96-9
(S)-1-Pyrrolidin-2-yl-methanol

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / K2CO3 / CH2Cl2 / 1.5 h 2: 79 percent / SOCl2 / CHCl3 / 4.5 h / 0 °C 3: 87 percent / NaN3, KI / dimethylformamide / 8 h 4: 75 percent / LiAlH4 / diethyl ether / 8 h View Scheme

: 7531-52-4
L-prolinamide

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / N,N-dimethyl-formamide / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 19.5 h / 20 °C / Inert atmosphere; Reflux View Scheme

: C19H23NO8S2

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Acidic conditions 2: hydrazine; zinc / 1,4-dioxane / 12 h / 20 °C / Large scale View Scheme

: (S)-1-ethyl-2-nitromethylpyrrolidine

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions

Conditions	Yield
With hydrazine; zinc In 1,4-dioxane at 20℃; for 12h; Reagent/catalyst; Large scale;	1014 g

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 135441-69-9
5-iodo-2,3-dimethoxybenzoyl chloride

: 107188-87-4
epidepride

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h;	100%
In dichloromethane at 20℃; Acylation;

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 7169-06-4
2,3-dimethoxybenzoyl chloride

: 107188-81-8
(-)-(S)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dimethoxybenzamide

Conditions

Conditions	Yield
In dichloromethane Ambient temperature;	100%
In dichloromethane Ambient temperature; Yield given;

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 108551-59-3
7-carboxy-5-ethyl-2,3-dihydrobenzofuran

: (S)-(-)-5-ethyl-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dihydrobenzofuran-7-carboxamide

Conditions

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide for 14h; Ambient temperature;	99%

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 149640-09-5
7-carboxy-5-(2-tetrahydropyranyloxyethyl)-2,3-dihydrobenzofuran

: (S)-(-)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-5-(2-tetrahydropyranyloxyethyl)-2,3-dihydrobenzofuran-7-carboxamide

Conditions

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide for 13h; Ambient temperature;	99%

: 81-08-3
2-sulfobenzoic acid cyclic anhydride

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 2-[((S)-1-Ethyl-pyrrolidin-2-ylmethyl)-carbamoyl]-benzenesulfonic acid

Conditions

Conditions	Yield
In benzene Heating;	97%

: 73219-91-7
2,6-dimethoxy-3,5-dichlorobenzoic acid

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 84225-94-5
(-)-A 32559

Conditions

Conditions	Yield
Stage #1: 2,6-dimethoxy-3,5-dichlorobenzoic acid With thionyl chloride at 80℃; for 2h; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃; Further stages.;	97%

: 49627-27-2
sulindac sulfide

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: (S,Z)-N-((1-ethylpyrrolidin-2-yl)methyl)-2-(5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)acetamide

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 20℃; Inert atmosphere;	97%

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 21615-34-9
2-Methoxybenzoyl chloride

: 96382-88-6
(S)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2-methoxybenzamide

Conditions

Conditions	Yield
In dichloromethane for 0.583333h;	96%

: C21H19FO2S

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: N-(((S)-1-ethylpyrrolidin-2-yl)methyl)-2-((Z)-5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)propanamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; Inert atmosphere;	95%

: 33045-52-2
methyl 2-methoxy-5-sulfamoyl-benzoate

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 15676-16-1, 23672-06-2, 23672-07-3, 23756-79-8
(S)-(-)-sulpiride

Conditions

Conditions	Yield
at 90 - 100℃; for 5h; Inert atmosphere;	93.8%
With hydrogenchloride In water; butan-1-ol	75%

: 38194-50-2
Sulindac

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: N-(((S)-1-ethylpyrrolidin-2-yl)methyl)-2-((Z)-5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; Inert atmosphere;	91%

: 33045-53-3
2-methoxy-5-sulfamoylbenzoic acid ethyl ester

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 15676-16-1, 23672-06-2, 23672-07-3, 23756-79-8
(S)-(-)-sulpiride

Conditions

Conditions	Yield
In isopropyl alcohol at 80℃; for 36h; Solvent; Temperature;	90.3%
In diethylene glycol at 80℃; for 48h;

: 3,6-Bis-benzyloxy-2-methoxy-benzoyl chloride

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 101460-68-8
(S)-3,6-Bis(benzyloxy)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2-methoxybenzamide

Conditions

Conditions	Yield
In chloroform at 50℃; for 0.5h;	90%
In dichloromethane Yield given;

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 136565-41-8
5-(3-Fluoro-propyl)-2,3-dimethoxy-benzoyl chloride

: 126247-33-4
FPMP

Conditions

Conditions	Yield
In dichloromethane for 0.25h; Ambient temperature;	90%

: 12092-47-6
di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: [Rh(cod)((1R,2R)-1,2-diphenylethylenediamine)]BF4

Conditions

Conditions	Yield
Stage #1: di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium With silver tetrafluoroborate In tetrahydrofuran for 1h; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In tetrahydrofuran for 1h;	90%

: 4-(4-benzyloxybutynyl)-2,3-dimethoxybenzoic acid

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: N-(5-(4-benzyloxybutynyl)-2,3-dimethoxybenzoyl)-(S)-(1-ethylpyrrolidin-2-yl) amine

Conditions

Conditions	Yield
Stage #1: 4-(4-benzyloxybutynyl)-2,3-dimethoxybenzoic acid With thionyl chloride In toluene at 60℃; for 1h; Inert atmosphere; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃; for 8h; Inert atmosphere; Cooling with ice;	88.6%

: chloro(1,5-cyclooctadiene)rhodium(I) dimer

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 2923-28-6
silver trifluoromethanesulfonate

: [Rh(cycloocta-1,5-diene)((-)-(S)-2-(aminomethyl)-1-ethylpyrrolidine)]CF3SO3

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: AgCl; (N2); standard Schlenk technique; Ag salt was added to soln. of Rh complex in THF; soln. was stirred at room temp. for 1 h; filtered; pyrrolidine derivative (1 equiv.) was added to filtrate; soln. was stirred for 1 h; concd. (vac.); hexane added; filtered; washed (hexane; Et2O); dried (vac.); elem. anal.;	88%

...Expand

: 12092-47-6
di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: [Rh(cod)((S)-2-aminomethyl-1-ethylpyrrolidine)]CF3SO3

Conditions

Conditions	Yield
Stage #1: di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium With silver trifluoromethanesulfonate In tetrahydrofuran for 1h; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In tetrahydrofuran for 1h;	88%

: C21H19FO3S

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: N-(((S)-1-ethylpyrrolidin-2-yl)methyl)-2-((Z)-5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)propanamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; Inert atmosphere;	88%

: 72517-23-8
5-bromo-2,3-dimethoxybenzoic acid

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 107188-74-9
[3H]-FLB 457

Conditions

Conditions	Yield
Stage #1: 5-bromo-2,3-dimethoxybenzoic acid With thionyl chloride In toluene at 60℃; for 1h; Inert atmosphere; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃; for 8h; Inert atmosphere; Cooling with ice;	87.5%

: 5-(5-benzyloxypentynyl)-2,3-dimethoxybenzoic acid

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: N-(5-(5-benzyloxypentynyl)-2,3-dimethoxybenzoyl)-(S)-(1-ethylpyrrolidin-2-yl)amine

Conditions

Conditions	Yield
Stage #1: 5-(5-benzyloxypentynyl)-2,3-dimethoxybenzoic acid With thionyl chloride In toluene at 60℃; for 1h; Inert atmosphere; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃; for 8h; Inert atmosphere; Cooling with ice;	85.2%

: 5-(6-benzyloxyhexynyl)-2,3-dimethoxybenzoic acid

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: N-(5-(6-benzyloxyhexynyl)-2,3-dimethoxybenzoyl)-(S)-(1-ethylpyrrolidin-2yl)amine

Conditions

Conditions	Yield
Stage #1: 5-(6-benzyloxyhexynyl)-2,3-dimethoxybenzoic acid With thionyl chloride In toluene at 60℃; for 1h; Inert atmosphere; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃; for 8h; Inert atmosphere; Cooling with ice;	85.2%

: 1097136-49-6
C19H9NO4

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 1097136-26-9
C26H23N3O3

Conditions

Conditions	Yield
In ethanol for 3h; Reflux;	85%

: 14121-49-4
benzothioxanthene-3,4-dicarboxylic anhydride

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 1097136-38-3
C25H22N2O2S

Conditions

Conditions	Yield
In ethanol for 3h; Reflux;	85%

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 674784-42-0
2-phenylthiazonaphthalic anhydride

: 1097136-44-1
C26H23N3O2S

Conditions

Conditions	Yield
In ethanol for 3h; Reflux;	85%

: 1466-76-8
2-6-dimethoxybenzoic acid

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 96947-76-1
(S)-(-)-N-<(ethyl-2-pyrrolidinyl)methyl>-2,6-dimethoxybenzamide

Conditions

Conditions	Yield
Stage #1: 2-6-dimethoxybenzoic acid With thionyl chloride In hexane for 2h; Reflux; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃;	84.5%
Stage #1: 2-6-dimethoxybenzoic acid With diatomite earth(at)IL/ZrCl4 (Lewis acidic ionic liquid immobilized on diatomite earth) In toluene for 0.0833333h; Green chemistry; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In toluene at 20℃; for 0.333333h; Sonication; Green chemistry;	80%

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 541-41-3
chloroformic acid ethyl ester

: (-)-Amisulpride

Conditions

Conditions	Yield
In acetone	84%

...Expand

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 97606-28-5
N-(N',N'-dimethylaminoethyl)benzo[b]thieno[2, 1-c]naphthalic anhydride

: 1097136-32-7
C25H22N2O2S

Conditions

Conditions	Yield
In ethanol for 3h; Reflux;	83%

: 14588-61-5
4-benzyloxy-3,5-dimethoxybenzoic acid chloride

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: C23H30N2O4

Conditions

Conditions	Yield
With sodium carbonate In toluene at 20℃; for 18h;	83%
With sodium carbonate In water; toluene at 20℃; for 18h;	66 mg

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 171805-81-5
2-(2-Fluoro-ethoxy)-5-iodo-3-methoxy-benzoyl chloride

: (S)-(-)-2-(2-fluoroethoxy)-5-iodo-3-methoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide

Conditions

Conditions	Yield
In dichloromethane for 0.333333h; Ambient temperature;	81%

(S)-2-(Aminomethyl)-1-ethylpyrrolidine Chemical Properties

Structure of 2-Pyrrolidinemethanamine,1-ethyl-, (2S)- (CAS NO.22795-99-9):

Empirical Formula: C₇H₁₆N₂
Molecular Weight: 128.2153
Index of Refraction: 1.468
Molar Refractivity: 39.56 cm³
Molar Volume: 142 cm³
Polarizability: 15.68×10^-24cm³
Surface Tension: 30.8 dyne/cm
Density: 0.902 g/cm³
Flash Point: 60.6 °C
Enthalpy of Vaporization: 39.85 kJ/mol
Boiling Point: 161.9 °C at 760 mmHg
Vapour Pressure: 2.22 mmHg at 25°C
Physical Appearance: Clear colorless to faintly yellow liquid
Product Categories: API intermediates;Glycidyl Compounds, etc. (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Chiral Building Blocks;Heterocyclic Building Blocks;Pyrrolidines

(S)-2-(Aminomethyl)-1-ethylpyrrolidine Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
R26:Very toxic by inhalation.
R36:Irritating to eyes.
R37:Irritating to respiratory system
R39:Danger of very serious irreversible effects.
RIDADR: UN 1993 3/PG 3
WGK Germany: 3

(S)-2-(Aminomethyl)-1-ethylpyrrolidine Specification

2-Pyrrolidinemethanamine,1-ethyl-, (2S)- , its cas register number is 22795-99-9. It also can be called -[(2S)-1-Ethyl-2-pyrrolidinyl]methanamine ; 1-[(2S)-1-Ethylpyrrolidin-2-yl]methanamin ; (S)-(-)-2-Aminomethyl-1-ethylpyrrolidine ; [(2S)-1-Ethylpyrrolidin-2-Yl]Methanamine ; 1-(1-Ethylpyrrolidin-2-yl)methanamine .

Product Name

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Synthetic route

(S)-2-(Aminomethyl)-1-ethylpyrrolidine Chemical Properties

(S)-2-(Aminomethyl)-1-ethylpyrrolidine Safety Profile

(S)-2-(Aminomethyl)-1-ethylpyrrolidine Specification

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