532-24-1

Basic information

• Product Name: Tropinone
• Synonyms: TIMTEC-BB SBB006924;8-Azabicyclo[3.2.1]octan-3-one, 8-methyl-;1-Methyl-2,6-ethanopiperidine-4-one;8-Methyl-3,6-epiminocycloheptane-1-one;Tropane-3-one;1αH,5αH-Tropan-3-one;NSC 118012;1αH,5αH-Tropan-3-one (8CI)
• CAS NO: 532-24-1
• Molecular Formula: C₈H₁₃NO
• Molecular Weight: 139.19
• EINECS: 208-530-6
• Product Categories: Pharmaceutical intermediates;Miscellaneous Biochemicals;chiral;Fused Ring Systems
• Mol File: 532-24-1.mol
• Article Data: 18

Chemical Properties

• Melting Point: 40-44 °C(lit.)
• Boiling Point: 113 °C25 mm Hg(lit.)
• Flash Point: 194 °F
• Appearance: brown/crystalline
• Density: 1.0268 (rough estimate)
• Vapor Pressure: 0.135mmHg at 25°C
• Refractive Index: 1.4598 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.93±0.20(Predicted)
• BRN: 2329
• CAS DataBase Reference: Tropinone(CAS DataBase Reference)
• NIST Chemistry Reference: Tropinone(532-24-1)
• EPA Substance Registry System: Tropinone(532-24-1)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-22-36/37/38
• Safety Statements: 23-24/25-36/37/39-26-22
• RIDADR: 1544
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 532-24-1(Hazardous Substances Data)

Usage

Chemical Properties

Tropinone is a white to light yellow crystal powder, It is an alkaloid and a precursor to a number of additional plant alkaloids. Tropinone is the first intermediate in the biosynthesis of the pharmacologically important tropane alkaloids that possesses the 8-azabicyclo[3.2.1]octane core bicyclic structure that defines this alkaloid class. Chemical synthesis of tropinone was achieved in 1901 but the mechanism of tropinone biosynthesis has remained elusive.

Uses

Tropinone is an oxidative product of Tropane, used to synthesize Morphine and Tropane alkaloids.

Preparation

The first synthesis of tropinone was by Richard Willst?tter in 1901. It started from the seemingly related cycloheptanone, but required many steps and had an overall yield of only 0.75%.Willst?tter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine. The 1917 synthesis by Robinson is considered a legend in total synthesis due to its simplicity and biomimetic approach. Tropinone is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, methyl amine and acetone dicarboxylic acid (or even acetone). The synthesis is a good example of a biomimetic reaction or biogenetic-type synthesis because biosynthesis makes use of the same building blocks. It also demonstrates a tandem reaction in a one-pot synthesis. Furthermore the yield of the synthesis was 17% and with subsequent improvements exceeded 90%.

InChI:InChI=1/C8H13NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-7H,2-5H2,1H3/p+1/t6-,7+

Synthetic route

cyclohepta-2,6-dienone (1192-93-4) + methylamine hydrochloride (593-51-1) → tropinone (532-24-1)

Conditions	Yield
With potassium carbonate In methanol at 25℃; for 2h;	72%

3-oxo-tropane-2,4-dicarboxylic acid dimethyl ester (100371-46-8) → (+/-)-2-(carbomethoxy)-3-tropinone (36127-17-0) + tropinone (532-24-1)

Conditions	Yield
With phosphate buffer In water at 20℃; for 24h; pH=8.0; Decarboxylation; demethoxycarbonylation;	A 55% B 13%

(+/-)-hygrine (45771-52-6) → tropinone (532-24-1) + 1-[1-Methyl-pyrrolidin-(2E)-ylidene]-propan-2-one

Conditions	Yield
With mercury(II) diacetate In acetic acid for 18h; Heating;	A 12% B 25%

acetonedicarboxylic acid (542-05-2) + butanedial (638-37-9) + methylamine hydrochloride (593-51-1) → tropinone (532-24-1) + 2-[1-methyl-5-(2-oxopropyl)pyrrolidin-2-yl]acetone (36295-25-7)

Conditions	Yield
With disodium hydrogenphosphate; water bei pH 6.8;

(1-methyl-pyrrolidine-2,5-diyl)-di-acetic acid diethyl ester (5690-89-1) → tropinone (532-24-1)

Conditions	Yield
With 4-methylisopropylbenzene; sodium at 160℃;
With xylene; sodium t-butanolate Erhitzen des jeweiligen Reaktionsprodukts mit wss. Schwefelsaeure oder Salzsaeure;

butanedial (638-37-9) + acetone (67-64-1) + methylamine (74-89-5) → tropinone (532-24-1)

Conditions	Yield
With water

butanedial (638-37-9) + diethyl 1,3-acetonedicarboxylate (105-50-0) + methylamine (74-89-5) → tropinone (532-24-1)

Conditions	Yield
Erhitzen der sauren Loesung des Reaktionsprodukts;

acetonedicarboxylic acid (542-05-2) + butanedial (638-37-9) + methylamine (74-89-5) → tropinone (532-24-1)

Conditions	Yield
in verduennter waessriger Loesung im pH-Bereich 3-11 bei ca. 3-taegiem Stehenlassen bei Raumtemperatur;
at 20 - 25℃; bei pH 3-11;

Tropanol (7432-10-2, 911648-75-4) → tropinone (532-24-1)

Conditions	Yield
elektrolytischen Oxydation in saurer oder swach alkalischer Loesung;

3-tropanol (120-29-6) → tropinone (532-24-1)

Conditions	Yield
With chromium(III) oxide; sulfuric acid at 0℃;
With chromic acid; acetic acid at 60 - 70℃;
With sulfuric acid; chromic acid at 50 - 55℃;

pseudotropine (135-97-7) → tropinone (532-24-1)

Conditions	Yield
With chromic acid; acetic acid at 60 - 70℃;
With sulfuric acid; permanganate(VII) ion at 10 - 12℃;
With lead dioxide at 60 - 70℃;
With potassium hexacyanoferrate(III)
With chromic acid; acetic acid at 60 - 70℃;

ecgonine (481-37-8) → tropinone (532-24-1)

Conditions	Yield
With sulfuric acid; chromic acid at 60℃; und anschliessendem Kochen mit Schwefelsaeure;

2β-bromo-8-methyl-8-azabicyclo<3.2.1>octan-3-one (62251-43-8, 62251-46-1) → tropinone (532-24-1)

Conditions	Yield
With K2CO3,H2/Ra Ni 28 In water under 3.3 Torr; for 0.5h;

3-nitroso-3-acetoxytropane → tropinone (532-24-1)

Conditions	Yield
With sulfuric acid Ambient temperature; Yield given;
In dichloromethane Product distribution; Ambient temperature; also on treatment with dilute H2SO4;

2α-bromotropan-3-one → tropinone (532-24-1)

Conditions	Yield
With K2CO3,H2/Ra Ni 28 In water under 3.3 Torr; for 0.5h;

3,6-Bis-benzenesulfonyl-cycloheptanone + methylamine (74-89-5) → tropinone (532-24-1)

Conditions	Yield
In methanol; water Yield given;

3-oxo-tropane-2-carboxylic acid ethyl ester (100055-81-0) + sulfuric acid (7664-93-9) → tropinone (532-24-1)

butanedial (638-37-9) + methylamine (74-89-5) + acetone-α.α'-dicarboxylate calcium → tropinone (532-24-1)

Conditions	Yield
Erhitzen der sauren Loesung des Reaktionsprodukts;

Tropanol (7432-10-2, 911648-75-4) + alkaline potassium ferricyanide solution → tropinone (532-24-1)

acetic acid (64-19-7) + Tropanol (7432-10-2, 911648-75-4) + chromic acid → tropinone (532-24-1)

Conditions	Yield
at 60 - 70℃;
at 60 - 70℃;

Tropanol (7432-10-2, 911648-75-4) + Cr2O3-H2SO4 → tropinone (532-24-1)

ecgonine (481-37-8) + Cr2O3-H2SO4 → tropinone (532-24-1)

sulfuric acid (7664-93-9) + Tropanol (7432-10-2, 911648-75-4) + lead dioxide → tropinone (532-24-1)

Conditions	Yield
at 60 - 70℃;

formaldehyd (50-00-0) + nortropinone → tropinone (532-24-1)

Conditions	Yield
With methanol anschliessenden Hydrieren des Reaktionsgemisches an Raney-Nickel;

Tropanol (7432-10-2, 911648-75-4) + potassium permanganate → tropinone (532-24-1)

Conditions	Yield
in schwefelsaurer Loesung;

sulfuric acid (7664-93-9) + Tropanol (7432-10-2, 911648-75-4) + potassium permanganate → tropinone (532-24-1)

Conditions	Yield
at 10℃;

Tropanol (7432-10-2, 911648-75-4) + potassium ferricyanide + soda alkaline → tropinone (532-24-1)

tropinone-carboxylic acid-(2)-ethyl ester → tropinone (532-24-1)

Conditions	Yield
With diluted acids
With diluted acids

hydrogenchloride (7647-01-0) + tropinone oxime (1515-26-0, 14587-46-3) + zinc → tropinone (532-24-1)

tropinone (532-24-1) → tropane (529-17-9)

Conditions	Yield
With hydrogenchloride; hydrogen; platinum(IV) oxide under 1.5 Torr; for 35h;	100%
With potassium hydroxide; hydrazine In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol for 8h; Wolff-Kischener reduction; Heating;

tropinone (532-24-1) → nortropinone (5632-84-8)

Conditions	Yield
Stage #1: tropinone With carbonochloridic acid 1-chloro-ethyl ester In 1,2-dichloro-ethane for 3h; Heating; Stage #2: In methanol for 5h; Heating;	100%
With DAOP(2+)*2BF4(1-); oxygen In acetonitrile at 20℃; Irradiation;	93%
With carbonochloridic acid 1-chloro-ethyl ester In methanol	88%

tropinone (532-24-1) → tropinone oxime (1515-26-0, 14587-46-3)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol for 1h; Reflux;	100%
With hydroxylamine hydrochloride; sodium acetate In ethanol Reflux;	90%
With pyridine; hydroxylamine hydrochloride In ethanol for 0.833333h; Heating / reflux;	66%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + tropinone (532-24-1) → ethyl (8-methyl-8-azabicyclo<3.2.1>oct-3-ylidene)acetate (2858-77-7)

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: tropinone In tetrahydrofuran at 20℃; Further stages.;	99.4%
With potassium hexamethylsilazane In tetrahydrofuran at 20 - 80℃; for 37h; Wadsworth-Emmons reaction;	62%

tropinone (532-24-1) → Tropanol (7432-10-2, 911648-75-4)

Conditions	Yield
With C15H18BF3; hydrogen; tert-butylimino-tri(pyrrolidino)phosphorane In tetrahydrofuran at 75℃; under 75007.5 Torr; for 24h; Glovebox;	96%
With C16H33Cl2CoN5P2; hydrogen; sodium t-butanolate In tert-Amyl alcohol at 20℃; under 15001.5 Torr; for 24h; Autoclave;	92%
With 2-methyl-propan-1-ol; sodium In toluene for 24h; Heating;	65%

tropinone (532-24-1) + chloroformic acid ethyl ester (541-41-3) → N-carbethoxytropinone (32499-64-2)

Conditions	Yield
With potassium carbonate In toluene Heating;	95%
With potassium carbonate; triethylamine In toluene Heating;	95%
With potassium carbonate In toluene Reflux;	92%

tropinone (532-24-1) → (+/-)-9-methyl-3,9-diazabicyclo[4.2.1]nonan-4-one (7309-42-4)

Conditions	Yield
Stage #1: tropinone With sodium azide; sulfuric acid In chloroform for 2h; Reflux; Stage #2: With potassium carbonate; potassium hydroxide In chloroform; water	95%
Stage #1: tropinone With sodium azide; sulfuric acid In chloroform for 2h; Reflux; Stage #2: With potassium carbonate; potassium hydroxide In chloroform; water for 0.166667h;	95%
Stage #1: tropinone With sodium azide; sulfuric acid In chloroform at -5 - 35℃; for 2h; Reflux; Stage #2: With potassium carbonate; potassium hydroxide In water	95%

tropinone (532-24-1) + methyl iodide (74-88-4) → 8,8-dimethyl-3-oxo-8-azonia-bicyclo[3.2.1]octane iodide (6690-08-0)

Conditions	Yield
In acetone at 20℃; for 1h;	92%
at 20℃; for 1h;	92%
In ethanol for 2h;	91%

pyridine-4-carbaldehyde (872-85-5) + tropinone (532-24-1) → (2E,4E)-8-methyl-2,4-bis((pyridin-4-yl)methylene)-8-aza-bicyclo[3.2.1]octan-3-one (1251531-74-4)

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 18h;	92%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + tropinone (532-24-1) → 8-Methyl-3-trifluoromethanesulfonyl-oxy-8-azabicyclo[3.2.1]oct-2-ene (893429-75-9, 893429-77-1, 183810-37-9)

Conditions	Yield
Stage #1: tropinone With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 3h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; Further stages.;	90%
Stage #1: tropinone With potassium hexamethylsilazane In tetrahydrofuran at -78℃; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃;	75%

tropinone (532-24-1) + acetaldehyde (75-07-0) → (1RS,2SR,1'SR,5SR)-2-(1'-hydroxyethyl)-tropinone

Conditions	Yield
Stage #1: tropinone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: acetaldehyde In tetrahydrofuran; hexane at -78℃; for 0.666667h; Aldol condensation; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane diastereoselective reaction;	87%

tropinone (532-24-1) + 3-bromo-4-(methoxymethoxy)benzaldehyde (162269-90-1) → C26H27Br2NO5

Conditions	Yield
With barium dihydroxide In methanol at 20℃; for 2h;	86.3%

Nonafluorobutanesulfonyl fluoride (375-72-4) + tropinone (532-24-1) → rac-8-methyl-8-azabicyclo[3.2.1]oct-2-en-3-yl nonaflate

Conditions	Yield
Stage #1: tropinone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - -50℃; for 0.5h; Stage #2: Nonafluorobutanesulfonyl fluoride In tetrahydrofuran; hexane at -78 - 20℃; for 17h; Further stages.;	86%

Nonafluorobutanesulfonyl fluoride (375-72-4) + tropinone (532-24-1) → 8-methyl-8-azabicyclo[3.2.1]oct-2-en-3-yl nonaflate

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 20℃;	86%

concentrated NH4 OH + 4-bromo-1,2-dichlorobenzene (18282-59-2) + tropinone (532-24-1) → 3-(3,4-dichloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol (189746-59-6)

Conditions	Yield
With hydrogenchloride; n-butyllithium In tetrahydrofuran; diethyl ether; water	86%

1.4-dibromobenzene (106-37-6) + tropinone (532-24-1) → 3-(4-bromophenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol

Conditions	Yield
Stage #1: 1.4-dibromobenzene; tropinone With n-butyllithium In tetrahydrofuran at -75 - -70℃; for 0.5h; Inert atmosphere; Stage #2: tropinone In tetrahydrofuran at -40℃; for 0.5h; Inert atmosphere;	85.2%

tropinone (532-24-1) + benzylamine (100-46-9) → 3-endo-benzylamino-8-methyl-8-azabicyclo[3.2.1]octane (101353-61-1)

Conditions	Yield
With sodium tetrahydroborate; 2-Ethylhexanoic acid In dichloromethane Ambient temperature;	85%
With ethanol; platinum at 50℃; Hydrogenation;
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane for 18h; Ambient temperature;
With ethanol; platinum at 50℃; Hydrogenation;

tropinone (532-24-1) → pseudotropine (135-97-7)

Conditions	Yield
With lithium borohydride In tetrahydrofuran a) -78 deg C, 6 h, b) RT, overnight;	85%
With 2-methyl-propan-1-ol; sodium; toluene
With lithium borohydride In tetrahydrofuran at -78℃;

tropinone (532-24-1) + benzene (71-43-2) → 3,3-diphenyl-N-methyl-8-azabicyclo[3.2.1]octane (67171-13-5)

Conditions	Yield
With trifluorormethanesulfonic acid at 20℃; for 3h; Substitution;	85%

tropinone (532-24-1) + 4-chlorobenzaldehyde (104-88-1) → 2,4-bis(4-chlorobenzylidene)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one (1121978-98-0)

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; Inert atmosphere;	85%

tropinone (532-24-1) + P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester (128833-03-4) → 3-[(3-bromophenyl)methylidene]-8-methyl-8-azabicyclo[3.2.1]octane (1177559-70-4)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 5h;	85%

3-pyridinecarboxaldehyde (500-22-1) + tropinone (532-24-1) → (2E,4E)-8-methyl-2,4-bis((pyridin-3-yl)methylene)-8-aza-bicyclo[3.2.1]octan-3-one (1251531-75-5)

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 18h;	85%

m-bromobenzoic aldehyde (3132-99-8) + tropinone (532-24-1) → C22H19Br2NO

Conditions	Yield
With sodium hydroxide In ethanol; water Cooling with ice;	84%

tropinone (532-24-1) → 3-endo-amino-8-methyl-8-azabicyclo[3.2.1.]octane bis-hydrochloride

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol; water at 20℃;	83%

2-phenyl-indole (948-65-2) + tropinone (532-24-1) → 3-(8-methyl-8-aza-bicyclo[3.2.1]oct-2-en-3-yl)-2-phenyl-1H-indole

Conditions	Yield
With phosphoric acid; acetic acid at 100℃;	82%

tropinone (532-24-1) + 4-methoxy-benzaldehyde (123-11-5) → (2E,4E)-2,4-bis(4-methoxy-benzylidene)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one (379669-36-0)

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; Inert atmosphere;	82%
With sodium hydroxide In ethanol at 20℃; for 0.5h;	32%

tropinone (532-24-1) + benzaldehyde (100-52-7) → C22H21NO

Conditions	Yield
With sodium hydroxide In ethanol; water Cooling with ice;	82%

trimethylsilyl cyanide (7677-24-9) + tropinone (532-24-1) → (3-Oxo-8-aza-bicyclo[3.2.1]oct-8-yl)-acetonitrile (131444-44-5)

Conditions	Yield
With oxygen; N,N'-dimethyl-2,7-diazapyrene bis(tetrafluoroborate) In acetonitrile at 20℃; for 4h; Irradiation; various other tertiary amines, other times;	81%
With oxygen; N,N'-dimethyl-2,7-diazapyrene bis(tetrafluoroborate) In acetonitrile at 20℃; for 4h; Irradiation;	81%

diacetyl-2-(4-N-allyl-3-thiosemicarbazonato)-3-(4-N-amino-3-thiosemicarbazonato)zinc(II) + tropinone (532-24-1) → diacetyl-2-(4-N-allyl-3-thiosemicarbazonato)-3-(4-N-tropimine-3-thiosemicarbazonato)zinc(II)

Conditions	Yield
In methanol 3-tropinone added to soln. of Zn complex in MeOH under stirring, mixt. heated at reflux for 12-16 h under N2, mixt. allowed to cool slowly to room temp.; ppt. filtered off, washed with cold MeOH and Et2O, dried under vac. at 80°C; elem. anal.;	81%

diethyl 1-cyanomethylphosphonate (2537-48-6) + tropinone (532-24-1) → 2-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetonitrile (91817-61-7)

Conditions	Yield
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.25h; Inert atmosphere; Stage #2: tropinone In tetrahydrofuran; mineral oil at 60℃; for 2h; Inert atmosphere;	80.7%
With sodium hydride In tetrahydrofuran at 25℃; for 2h;

Upstream product

• 5690-89-1 (1-methyl-pyrrolidine-2,5-diyl)-di-acetic acid diethyl ester 
• 481-37-8 ecgonine 
• 62251-43-8 2β-bromo-8-methyl-8-azabicyclo<3.2.1>octan-3-one 
• 74-89-5 methylamine 
• 542-05-2 acetonedicarboxylic acid 
• 638-37-9 butanedial 
• 7732-18-5 water 
• 1515-26-0 tropinone oxime 
• 121846-51-3 tropan-3-one silyl enol ether 
• 34160-24-2 2,5-dimethoxytetrahydrofuran 
• 100-46-9 benzylamine 
• 5632-84-8 8-azabicyclo[3.2.1]octan-3-one 
• 74-88-4 methyl iodide 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 

Downstream Products

• 72362-45-9 (-)-ent-Isobellendine 
• 32152-73-1 (+/-)-Bellendine 
• 36127-17-0 methyl 8-methyl-3-oxo-8-azabicyclo<3.2.1>octan-2-carboxylate 
• 135-97-7 pseudotropine 
• 464-72-2 tetraphenylethane-1,2-diol 
• 63930-13-2 endo-3-(N-phenylamino)tropane 
• 101353-61-1 3-endo-benzylamino-8-methyl-8-azabicyclo[3.2.1]octane 
• 145817-65-8 N-(3-Chloro-phenyl)-N'-((1R,3S,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-ethane-1,2-diamine 

Relevant articles and documents

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