[ CAS No. 768-94-5 ] {[proInfo.proName]}

Name: 768-94-5|Adamantan-1-amine|99%
Brand: Ambeed
SKU: A2667917
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Quality Control of [ 768-94-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 768-94-5 ]

Product Details of [ 768-94-5 ]

CAS No. :	768-94-5	MDL No. :
Formula :	C₁₀H₁₇N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	151.25	Pubchem ID :	-
Synonyms :	1-Aminoadamantane;1-Adamantanamine;1-Adamantylamine	Chemical Name :	Adamantan-1-amine

Calculated chemistry of [ 768-94-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.59
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	2.44
Log Po/w (WLOGP) :	1.91
Log Po/w (MLOGP) :	2.45
Log Po/w (SILICOS-IT) :	1.91
Consensus Log Po/w :	2.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.31
Solubility :	0.732 mg/ml ; 0.00484 mol/l
Class :	Soluble
Log S (Ali) :	-2.63
Solubility :	0.355 mg/ml ; 0.00235 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.57
Solubility :	4.08 mg/ml ; 0.027 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.49

Safety of [ 768-94-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 768-94-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 768-94-5 ]
Downstream synthetic route of [ 768-94-5 ]

[ 768-94-5 ] Synthesis Path-Upstream 1~9

1
[ 124-38-9 ]
[ 768-94-5 ]
[ 3717-38-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With diphenylsilane; caesium carbonate In acetonitrile at 80℃; for 72 h; Schlenk technique; Inert atmosphere	1) In a glove box, 0.25 mmol of amantadine,6 equiv (1.5 mmol) of diphenylsilane,10 molpercent (based on amantadine) Cesium carbonate,1.6 ml of acetonitrile solvent was added to 50 ml of a Schlenk tube protected with N2. 2) The N2 in the Schlenk tube was replaced by CO2 in the double-row tube under refrigeration vacuum operation,The pressure of CO2 is 1 bar. 3) using said cesium carbonate as a catalyst,Said carbon dioxide being a C1 source,The diphenylsilane is used as a reducing agent,The amantadine was reacted in an acetonitrile solvent at 80 ° C for 72 hours. 4) After completion of the reaction,To the Schlenk tube was added 0.2 mmol of ferrocene as the internal magnetic standard. 5) By Bruker NMR analysis,The NMR spectra of the resulting product are consistent with the literature (P. Besenius, P. A. G. Cormack, R. F. Ludlow, S. Otto, D. C. Sherrington, Chem. Commun. 2008,In the report of the corresponding pure substance spectrum consistent,In this embodimentN-methylamantanamineYield> 95percent.

Reference： [1] Patent: CN105753715, 2016, A, . Location in patent: Paragraph 0029; 0030; 0031; 0032; 0033; 0034; 0035
[2] ACS Catalysis, 2016, vol. 6, # 11, p. 7876 - 7881

2
[ 124-38-9 ]
[ 768-94-5 ]
[ 3717-40-6 ]
[ 3717-38-2 ]

Yield	Reaction Conditions	Operation in experiment
55%	With hydrogen In hexane at 140℃; for 7 h; Autoclave; Inert atmosphere	To a volume of 50 mL of Hastelloy autoclave was placed 10 mL of solvent n-hexane,1 mmol of amantadine,A certain amount of Au / Al2O3 catalyst (containing 5μmol)The autoclave was sealed and the inside of the autoclave was replaced with nitrogen three times,And then into the 1MPa of CO2 gas and 3MPa of H2,Keep the kettle gas pressure at 4MPa,Placed on the chassis with aluminum block on the magnetic stirrer,So that the temperature quickly rose to 140 ,Open the magnetic stirring,Stirring at 1000 rpm for 7 hours,After cooling, add a certain amount of n-octane as the internal standard,Using gas chromatography (FID detector),N-methylamine adamantine yield was 55percentThe yield of N, N-dimethyl-amantadine was 45percentNo other byproducts are generated.

Reference： [1] Patent: CN106316866, 2017, A, . Location in patent: Paragraph 0143; 0144

3
[ 768-94-5 ]
[ 74-88-4 ]
[ 3717-38-2 ]

Reference： [1] Chemical Communications, 2008, # 24, p. 2809 - 2811

4
[ 67-56-1 ]
[ 768-94-5 ]
[ 3717-40-6 ]
[ 3717-38-2 ]

Yield	Reaction Conditions	Operation in experiment
37 %Chromat.	at 150℃; for 5 h; Autoclave	6.0 mg (0.01 mmol) of complex 1 produced in Reference Example 1 and 303 mg (2 mmol) of 1-adamantylamine were added to a 100 ml stainless autoclave, nitrogen substitution was conducted, and 2 ml of methanol was then added thereto. Next, 1.1 ml (1.2 mmol) of 1.13 M methanol solution of NaOMe was added, and the mixture was then stirred at 150° C. for 5 hours. After cooling, the reactant was analyzed by GC, and N-methyladamantylamine was obtained at a GC yield of 19percent and N,N-dimethyladamantylamine was obtained at a GC yield of 37percent.

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 21, p. 6166 - 6170[2] Angew. Chem., 2018, vol. 130, p. 6274 - 6278,5
[3] Patent: US2016/9632, 2016, A1, . Location in patent: Paragraph 0186; 0187

5
[ 50-00-0 ]
[ 768-94-5 ]
[ 3717-38-2 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 43, p. 7680 - 7682

6
[ 768-94-5 ]
[ 3717-38-2 ]

Reference： [1] Farmaco, 2001, vol. 56, # 3, p. 181 - 189
[2] Chemische Berichte, 1994, vol. 127, # 8, p. 1517 - 1522

7
[ 768-94-5 ]
[ 702-82-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: With sulfuric acid; nitric acid In water at 5 - 25℃; Stage #2: at 0 - 40℃; for 1 h;	Example 1: Preparation of 3-amino-adamantan-l-ol (0099) In a clean and dry 5.0 L 4 necks RBF equipped with liquid addition funnel, TP. Charged cone, sulphuric acid (300 mL, 2 V) and cooled the reaction mass to 5-10 °C. To the cooled mass 1-adamantyl amine (150 g, 1 eq.) was added lot wise at 5-10 °C. After complete addition, stirred the reaction mass to get clear (slightly hazy) solution and maintained the reaction mass at 5-15 °C. Meanwhile a nitrating mixture was prepared by adding 150 mL of 65-70 percent nitric acid to 450 mL cone, sulphuric acid maintaining temperature at 0-10 °C). The nitrating mixture was added to the reaction mass maintaining reaction temperature at 20 ± 5 °C. After the addition was over, stirred the reaction mass at 20 ± 5°C for 3 to 5 h. Completion of the reaction was confirmed by GC. The reaction mass was cooled to 0 - 5 °C and added water (150 mL, I V) to the reaction mass maintaining 0-20 °C and again cooled reaction mass to 5-10 °C. Second lot of water (300 mL, 2 V) was added to the reaction mass maintaining 5-20 °C. The reaction mass was cooled again to 5-10 °C and added third lot of water (1050 mL, 7 V) to the reaction mass maintaining 5-20 °C. After complete addition of water the reaction mass was cooled to 0-5 °C and added 50 percent NaOH solution maintaining 0- 40 °C and stirred for 1 h at 35-40 °C. Filtered the solid obtained and washed the cake with water (150 mL, IV). Wet weight: 1 185 g. The wet cake was dried under reduced pressure at 60-70 °C. Mixed the above dried solid with IPA (750 mL, 5 V w.r.t. adamantly amine) and heated at 50 - 60°C and maintained for 1 h. Then cooled reaction mass to 20-25°C and maintained at 20-25°C for 1 h. Filtered the solid obtained and wash with IPA (150 mL, 1 V). Distilled around 600 mL, 4 - 4.5 V of IPA from reaction mass under reduced pressure and cooled the residual reaction mass to 40-45°C. Added cyclohexane (1200 mL, 8 V) to reaction mass and heated to 50-55°C. Applied 200-250 Torr vacuum slowly to the reaction mass and distilled cyclohexane (900 mL, 6 V) from reaction mass under reduced pressure. Filtered the solid and wash with cyclohexane (150 mL, IV) Unload solid and dry it for 10-12 h under reduced pressure at 60°C. Yield range: 90percent; GC purity > 98percent; melting point: 265°C; 1H NMR (CDC1₃, 400 MHz) δ: 1.35-1.48 (m, 14H, 6xCH₂, l NH₂); 2.08 (brs, 2H, 2*CH); 4.36 (s, ΙΗ, ΟΗ).
81%	at 0 - 10℃; for 2 h;	To a round bottom flask containing compound 13 (100mg, 0.53mmol) a mixture of concentrated sulfuric acid (2mL, 37.1mmol) and concentrated nitric acid (0.2mL, 4.46mmol) was added at 0°C. The mixture was left to stir for two hours at 10°C. Ice-cold water was then carefully added to the reaction mixture, following this addition the reaction mixture was made basic using solid sodium hydroxide until precipitation could be seen. The solution was thereafter filtered, and the wet solid collected and dissolved in DCM and left to stir for 30min. Next, the solid was removed from the solution by filtration and washed with DCM. The DCM-solution containing 14 was concentrated in vacuo to afford compound 14 (70mg, yield 81percent). ¹H NMR (CDCl₃ 300MHz) δ: 2.24–2.16 (m, 2H), 1.62–1.58 (m, 4H), 1.54–1.50 (m, 2H), 1.49–1.43(m, 6H). ¹³C NMR (CDCl₃, 75.4MHz) δ: 69.6 (HOC), 53.9, 50.5, 44.9, 44.2, 34.9, 31.1 (aliphatic C).

Reference： [1] Patent: WO2015/128718, 2015, A1, . Location in patent: Page/Page column 15
[2] Tetrahedron, 2018, vol. 74, # 24, p. 2905 - 2913
[3] Russian Journal of Organic Chemistry, 2009, vol. 45, # 8, p. 1137 - 1142

8
[ 768-94-5 ]
[ 665-66-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydroxylamine hydrochloride In ethanol for 2 h; Reflux	General procedure: To a 25-mL round-bottomed flask containing ammonium chloride (0.54 g, 10 mmol) was added ethanol (3 mL) followed by the requisite amine (10 mmol). The mixture was magnetically stirred and refluxed for 2 h. The solvent was then removed by rotary evaporation affording the hydrochloride salt as a solid invariably in quantitative yield.

Reference： [1] Synthetic Communications, 2015, vol. 45, # 22, p. 2601 - 2607
[2] Patent: WO2007/96124, 2007, A1, . Location in patent: Page/Page column 15-16
[3] Russian Journal of Organic Chemistry, 2015, vol. 51, # 12, p. 1703 - 1709[4] Zh. Org. Khim., 2015, vol. 51, # 12, p. 1737 - 1743,7

9
[ 768-94-5 ]
[ 1032564-18-3 ]

Reference： [1] Patent: WO2011/101861, 2011, A1,
[2] Patent: WO2015/128718, 2015, A1,

[ 768-94-5 ] Synthesis Path-Downstream 1~88

1
[ 5577-13-9 ]
[ 768-94-5 ]
[ 17822-61-6 ]

Reference： [1]Journal of Medicinal Chemistry,1963,vol. 6,p. 760 - 763

2
[ 13726-16-4 ]
[ 768-94-5 ]
Adamantan-1-yl-(4-chloro-3-methoxy-benzyl)-amine [ No CAS ]

Reference： [1]Patent: AT335420,1976,
Patent: DE2403138,1975,
Chem.Abstr.,1975,vol. 83

3
[ 10226-29-6 ]
[ 768-94-5 ]
6-(adamantan-1-yl)aminohexan-2-one [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie,1986,vol. 41,p. 1323 - 1328

4
[ 5511-18-2 ]
[ 768-94-5 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 4272 - 4276

5
[ 768-94-5 ]
[ 59-05-2 ]
[ 77410-21-0 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 559 - 567

6
[ 17702-83-9 ]
[ 768-94-5 ]
[ 206448-74-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 575 - 580

7
[ 768-94-5 ]
[ 24566-80-1 ]
[ 206448-76-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 575 - 580

8
[ 41731-83-3 ]
[ 768-94-5 ]
ethyl 2-(1-adamantylamino)-1,3-thiazole-5-carboxylate [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 353 - 356

9
[ 5417-17-4 ]
[ 768-94-5 ]
1-[(2-chloro-3,4-dimethoxybenzylidene)amino]adamantane [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2002,vol. 52,p. 778 - 781

10
[ 768-94-5 ]
[ 207557-35-5 ]
1-[(1-adamantylamino)acetyl]-2-pyrrolidinecarbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2774 - 2789

11
[ 768-94-5 ]
[ 148870-57-9 ]
[ 847737-86-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 1211 - 1220

12
[ 23911-25-3 ]
[ 768-94-5 ]
EDTA bis-1-adamantanylamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 5728 - 5734

13
[ 30169-25-6 ]
[ 768-94-5 ]
[ 484024-96-6 ]

Reference： [1]Russian Journal of Organic Chemistry,2006,vol. 42,p. 757 - 765

14
[ 1709-71-3 ]
[ 768-94-5 ]
2-methyl-acrylic acid 3-[3-(adamantan-1-yl-{2-[2-hydroxy-3-(2-methyl-acryloyloxy)-propoxycarbonyl]-ethyl}-amino)-propionyloxy]-2-hydroxy-propyl ester [ No CAS ]

Reference： [1]Macromolecules,2004,vol. 37,p. 3231 - 3238

15
[ 1835-65-0 ]
[ 768-94-5 ]
4-(1-adamantylamino)-3,5,6-trifluorophthalonitrile [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2006,vol. 84,p. 1380 - 1387

16
[ 1835-65-0 ]
[ 768-94-5 ]
4,5-di(1-adamantylamino)-3,6-difluorophthalonitrile [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2006,vol. 84,p. 1380 - 1387

17
[ 4744-50-7 ]
[ 768-94-5 ]
C₆H₂N₂O₂NC₁₀H₁₅ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 614 - 626

18
[ 4664-00-0 ]
[ 768-94-5 ]
C₇H₃NO₂NC₁₀H₁₅ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 614 - 626

19
[ 50-00-0 ]
[ 768-94-5 ]
[ 3717-38-2 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 7680 - 7682

20
[ 768-94-5 ]
[ 3717-38-2 ]

Reference： [1]Il Farmaco,2001,vol. 56,p. 181 - 189
[2]Chemische Berichte,1994,vol. 127,p. 1517 - 1522

21
[ 35265-83-9 ]
[ 768-94-5 ]
4-(1-adamantylamino)-2-chloro-7-methylthieno[3,2-d]pyrimidine [ No CAS ]

Reference： [1]Patent: US6339089,2002,B2 .Location in patent: Referential example 29

22
[ 768-94-5 ]
[ 37784-17-1 ]
tert-butyl (2R)-2-[(adamantan-1-yl)carbamoyl]pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With 4-methyl-morpholine; dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	Prep (9a): tert-butyl-(2R)-2-[(l-adamantylamino)carbonyl]pyrrolidine-l-carboxylate <strong>[37784-17-1]N-(tert-butoxycarbonyl)-D-proline</strong> (1.00g, 5.65 mmol), EDC (982 mg, 5.12 mmol), HOBt (692 mg, 5.12 mmol), DMAP (28 mg, 0.23 mmol), and 1-adamanyl amine (1.06 g, 6.98 mmol) were charged into a round bottom flask. CH2CI2 (25 mL) was added to dissolve the reagents followed by NMM (1.02 mL, 9.3 mL). The resultant solution was stirred at temperature of about 20 C overnight. The solution was concentrated in vacuo and the residue was partitioned between EtOAc (400 mL) and 0.5 N HCI (40 mL). The organic layer was separated and washed with 0.5 N HCI (40 mL), brine (40 mL), saturated NaHC03 (twice with 40 mL), brine (40 mL), dried (MgS04), filtered, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexanes/EtOAc (5-50%) to afford the title compound (1.7g, 105% yield). ¹H NMR (400 MHz, DMSO-D6) No. ppm 1.32 - 1.39 (10 H, m) 1.56 - 1.64 (6 H, m) 1.66 - 1.80 (3 H, m) 1.87 - 1.94 (6 H, s) 1.96 - 2.07 (4 H, m) 3.20 - 3.28 (1 H, m) 3.94 - 4.05 (1 H, m) 7.21 (1 H, s); LCMS (M+1 ): 349.

Reference： [1]Patent: WO2005/108359,2005,A1 .Location in patent: Page/Page column 48
[2]ChemMedChem,2020,vol. 15,p. 839 - 850

23
[ 35265-83-9 ]
[ 768-94-5 ]
[ 221043-49-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide;	Reference Example 29 4-(1-Adamantylamino)-2-chloro-7-methylthieno[3,2-d] pyrimidine In DMF was dissolved 700 mg (3.2 mmol) of <strong>[35265-83-9]2,4-dichloro-7-methylthieno[3,2-d]pyrimidine</strong>, and then an aqueous solution of 1.13 g (7.5 mmol) of 1-adamantaneamine was added dropwise to the resulting solution under ice cooling over 5 minutes. The reaction mixture was stirred at 0 C. for one hour and then allowed to resume room temperature, followed by stirring for one hour. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml*3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane={fraction (1/10)}) to give 1.10 g (yield: 100%) of the title compound. NMR (delta, CDCl3): 1.67-1.78 (7H, m), 2.08-2.23 (8H, m), 2.40 (3H, s), 4.61 (1H, br), 7.38 (1H, s)

Reference： [1]Patent: US2001/6969,2001,A1

24
[ 869-07-8 ]
[ 32618-85-2 ]
[ 768-94-5 ]
[ 221043-30-7 ]

Yield	Reaction Conditions	Operation in experiment
90 mg (20.7%)	With triethylamine; trichlorophosphate; In water; acetonitrile;	Reference Example 15 4-(1-Adamantylamino)-2-chloro-6-nitroquinazoline To 250 mg (1.21 mmol) of <strong>[32618-85-2]6-nitroquinazoline-2,4(1H,3H)-dione</strong> were added 5.00 ml (53.64 mmol) of phosphorus oxychloride and 0.18 ml (1.21 mmol) of diisopropylformamide, and the resulting mixture was subjected to heating under reflux for 24 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 5 ml of acetonitrile, followed by addition of 183 mg (1.21 mmol) of 1-adamantylamine and 0.84 ml (6.05 mmol) of triethylamine under ice cooling and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 90 mg (20.7%) of the title compound. NMR (delta, CDCl3): 1.75-1.82 (6H, m), 2.22 (3H, br), 2.28-2.32 (6H, m), 5.83 (1H, br s), 7.82 (1H, d, J=9 Hz), 8.48 (1H, dd, J=9 Hz, 2 Hz), 8.60 (1H, d, J=2 Hz)

Reference： [1]Patent: US2001/6969,2001,A1

25
[ 126-83-0 ]
[ 768-94-5 ]
3-(adamantan-1-ylamino)-2-hydroxy-1-propanesulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; water; at 80℃;	Preparation of 4-(adamantan-1-ylamino)-2-hydroxy-1-propanesulfonic acid (Compound KB); 1-adamantaneamine hydrochloride (2.67 g, 14.2 mmol) was treated with 1N NaOH (20 mL) and CH2Cl2 (3×20 mL). The organic extracts were combined, dried with Na2SO4, filtered, evaporated under reduced pressure and dried in vacuo. To an 80 C. solution of 1-adamantanamine(2.15 g, 14.2 mmol) in 1,4-dioxane (10 mL) and water (5 mL) was added via syringe pump (1 h addition) a solution of 3-chloro-2-hydroxy-propanesulfonic acid, sodium salt (1.93 g, 9.7 mmol) in 1,4-dioxane (0.5 mL) and water (10 mL). The solution was stirred at reflux overnight. The reaction was cooled to room temperature. The solvent was evaporated under reduced pressure. The solid was suspended in 25% acetone/EtOH. The mixture was heated to reflux for 1 minute. The solid was collected by filtration. The pure product crystallized in the filtrate. The product was filtered, washed with EtOH (2×10 mL), dissolved in water and lyophilized. Yield: 15%. 1H NMR (D2O, 500 MHz) delta ppm 4.18 (m, 1H), 3.22 (m, 1H), 3.01 (m, 2H), 2.94 (m, 1H), 2.06 (s, 3H), 1.77 (m, 7H), 1.61 (d, 3H), 1.53 (m, 3H). 13C (D2O, 125 MHz) delta ppm 64.23, 57.99, 55.05, 44.10, 38.10, 35.07, 29.03. ES-MS 288 (M-Na (23)).

Reference： [1]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 146

26
[ 21806-61-1 ]
[ 768-94-5 ]
(1Z)-3-(1-adamantylamino)prop-1-ene-1-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	In tetrahydrofuran; for 6h;Heating / reflux;	Preparation of (1Z)-(3-(1-adamantylamino)prop-1-ene-1-sulfonic acid (Compound N21); To a solution of 1,3-prop-1-ene sultone (obtained in step 3 in the preparation of Compound N20, 360 mg, 3 mmol) in THF (5 mL) was added 1-adamantylamine (545 mg, 3.6 mmol). The reaction mixture was refluxed for 6 h, and then concentrated to dryness. The residual solid was suspended in a solvent mixture of EtOH and ether (2.5 mL/2.5 mL), heated under reflux for 15 minutes, and cooled to room temperature. The solid material was collected by filtration, washed with ether, and dried; providing the title compound (130 mg, 22%); 1H NMR (500 MHz, D2O) delta 1.40-1.70 (m, 12H), 2.00 (m, 3H), 3.7 (d, J=7.0 Hz, 2H), 5.90 (m, 1H), 6.30 (d, J=11.0 Hz, 1H). 13C NMR (125 MHz, D2O) delta 28.95, 29.23, 35.05, 35.68, 36.67, 40.05, 40.75, 128.00, 132.98. ES-MS 270 (M-1).

Reference： [1]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 174

27
[ 665-66-7 ]
[ 768-94-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium chloride; sodium hydroxide; In water;	General procedure: Initially, its was necessary to neutralize atdH and mtnH and thus eliminate the chloride ions to avoid interference in the synthesis of the silver complexes. So, 2.0mmol of atdH (375.4mg) were dissolved in 24mL of H2O and the solution was treated with 16.0mL of a 5% aqueous solution of sodium hydroxide (NaOH) and 1.3g of sodium chloride (NaCl). The reaction mixture was submitted to extraction (4×) with 10.0mL of dichloromethane (CH2Cl2). A portion of anhydrous sodium carbonate (Na2CO3) was added to the organic fraction to remove water and filtered afterwards. The solvent was removed in a rotary evaporator. Yield 94% (284.3mg). The same process was performed for mtnH, but adjusted for 1.14mmol (245mg). Yield 56.8% (116.2mg).
	With sodium hydroxide; In water;	Preparation of 4-(adamantyl)amino-2-butanesulfonic acid (Compound JH); 1-adamantaneamine hydrochloride (2.51 g, 13.3 mmol) was treated with 1N NaOH (20 mL) and CH2Cl2 (3×20 mL). The organic extracts were combined, dried with Na2SO4, filtered, evaporated under reduced pressure and dried in vacuo. To a solution of 2-adamantanamine (1.99 g, 13.1 mmol) in acetonitrile (15 mL) was added 2,4-butane sultone (1.87 g, 13.8 mmol). The solution was stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with acetonitrile (3×25 mL) and dried in vacuo. 1H NMR (DMSO, 500 MHz) delta ppm 8.53 (s (broad), 1H), 3.33 (m, 2H), 2.61 (m, 1H), 2.10 (s, 3H), 1.93 (m, 1H), 1.77 (m, 7H), 1.61 (m, 6H), 1.12 (d, 1H, J=6.8 Hz). 13C (DMSO, 125 MHz) delta ppm 56.20, 53.34, 35.85, 29.75, 29.04, 17.206. ES-MS 288 (M+1).; Preparation of 4-(adamantyl)amino-1-butanesulfonic acid (Compound LI); 1-adamantaneamine hydrochloride (2.67 g, 13.3 mmol) was treated with 1N NaOH (20 mL) and CH2Cl2 (3×20 mL). The biphasic solution was shaken. The organic extracts were combined, dried with Na2SO4, filtered, evaporated under reduced pressure and dried in vacuo. To a solution of 2-adamantanamine (1.87 g, 12.4 mmol) in tetrahydrofuran (THF, 15 mL) was added 1,4-butane sultone (1.76 g, 13.0 mmol). The solution was stirred at reflux overnight. The reaction was cooled to room temperature. The solid was collected by filtration, washed with THF (1×15 mL) and dried in vacuo. A suspension of the solid in EtOH (25 mL) was stirred at reflux for 1 hour. The warm mixture was filtered. The solid was dried in vacuo. 1H NMR (D2O, 500 MHz) delta ppm 2.92 (m, 2H), 2.82 (m, 1H), 2.05 (s, 3H), 1.75 (s, 6H), 1.63 (m, 6H), 1.52 (m, 3H). 13C (D2O, 125 MHz) delta ppm 57.62, 50.30, 39.03, 38.14, 35.09, 28.98, 25.25, 21.63. ES-MS 288 (M+1).; Preparation of 4-(adamantan-1-ylamino)-2-hydroxy-1-propanesulfonic acid (Compound KB); 1-adamantaneamine hydrochloride (2.67 g, 14.2 mmol) was treated with 1N NaOH (20 mL) and CH2Cl2 (3×20 mL). The organic extracts were combined, dried with Na2SO4, filtered, evaporated under reduced pressure and dried in vacuo. To an 80 C. solution of 1-adamantanamine(2.15 g, 14.2 mmol) in 1,4-dioxane (10 mL) and water (5 mL) was added via syringe pump (1 h addition) a solution of 3-chloro-2-hydroxy-propanesulfonic acid, sodium salt (1.93 g, 9.7 mmol) in 1,4-dioxane (0.5 mL) and water (10 mL). The solution was stirred at reflux overnight. The reaction was cooled to room temperature. The solvent was evaporated under reduced pressure. The solid was suspended in 25% acetone/EtOH. The mixture was heated to reflux for 1 minute. The solid was collected by filtration. The pure product crystallized in the filtrate. The product was filtered, washed with EtOH (2×10 mL), dissolved in water and lyophilized. Yield: 15%. 1H NMR (D2O, 500 MHz) delta ppm 4.18 (m, 1H), 3.22 (m, 1H), 3.01 (m, 2H), 2.94 (m, 1H), 2.06 (s, 3H), 1.77 (m, 7H), 1.61 (d, 3H), 1.53 (m, 3H). 13C (D2O, 125 MHz) delta ppm 64.23, 57.99, 55.05, 44.10, 38.10, 35.07, 29.03. ES-MS 288 (M-Na (23)).
	With sodium hydroxide; In propan-1-ol; water; at 50℃; for 1h;	Reflux condenser,thermometer,In a 500 ml three-necked flask equipped with a stirrer,30 g of 2-propanol was charged,Under stirring, 30.0 g (0.16 mol) of 1-aminoadamantane hydrochloride (molecular weight: 187.1) was added. After heating the reaction system to 50 C.,14.0 g (0.17 mol) of a 48% by mass sodium hydroxide aqueous solution was slowly added dropwise, and the mixture was stirred for 1 hour to perform a dehydrochlorination reaction.

	With sodium carbonate; sodium hydroxide; In water; for 0.5h;pH 10;	The process for preparing amantadine free amines from <strong>[665-66-7]amantadine hydrochloride</strong>,The reaction vessel was charged with 200 L of water and 50 Kg of <strong>[665-66-7]amantadine hydrochloride</strong>,Stirring evenly, with sodium hydroxide or sodium carbonate to adjust the pH value of 10; precipitation of solid,Continue stirring 0. 5h, filtration, washing, drying,To obtain amantadine free amine pure.
	With sodium hydroxide; In water; isopropyl alcohol; at 50℃; for 1h;	A reflux condenser, a thermometer,Into a 500 ml three-necked flask equipped with a stirrer, 30 g of 2-propanol was placed,Under stirring, 30.0 g of 1-aminoadamantane hydrochloride (molecular weight: 187.1)(0.16 mol) was added. After raising the temperature of the reaction system to 50 C., 14.0 g (0.17 mol) of a 48% by mass sodium hydroxide aqueous solution was slowly added dropwise and the mixture was stirred for 1 hour to perform a dehydrochlorination reaction.
	With sodium hydroxide; In water; for 0.5h;	To a solution of 2 g of <strong>[665-66-7]amantadine hydrochloride</strong> (10.67 mmol) in 50 ml of deionized water,An aqueous solution of 5 g / 10 mL of sodium hydroxide was added,Immediately produce white precipitate,Stirring was continued for 30 minutes to allow the <strong>[665-66-7]amantadine hydrochloride</strong> to be fully deprotonated.The resulting solution was extracted with 200 ml of dichloromethane,Three times,After which the organic phase was dried over anhydrous sodium sulfate,After decompression,The filtrate was collected and evaporated to give white solid amantadine.
	With sodium hydroxide; In methanol; for 2h;Heating;	1-Aminoadamantane hydrochloridewas added to 200mL ofmethanolcontaining 8 g of sodium hydroxide, and the solution was stirredwith heating for 2 h. Then, the solventwas removed by rotary evaporationand the residuewaswashed at least thricewithwater to recover 1-aminoadamantane as a white solid.
	With potassium hydroxide; In ethanol; for 0.166667h;	<strong>[665-66-7]Amantadine hydrochloride</strong> (563 mg, 3.0 mmol) and potassium hydroxide (168 mg,3.0 mmol) in 50 mL anhydrous ethanol were stirred for 10 min and white precipitates (KCl) were filtered out. Then the transparent liquid was added dropwise to a solutionof 3,5-dihalosalicylaldehydes (haloCl, Br, I; 382, 560, 748 mg; 2.0 mmol) in 30 mLanhydrous ethanol. The mixture was refluxed for 1 h and then cooled to room temperature.The yellow Schiff base precipitates were collected after 1 week of slow solventevaporation.

Reference： [1]Polyhedron,2019,vol. 173
[2]Chemistry - A European Journal,2008,vol. 14,p. 4551 - 4561
[3]Angewandte Chemie - International Edition,2010,vol. 49,p. 3920 - 3924
[4]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 142; 145-146
[5]Synthetic Communications,2013,vol. 43,p. 1727 - 1733
[6]Journal of Medicinal Chemistry,2013,vol. 56,p. 9725 - 9736
[7]Journal of Pharmaceutical Sciences,2014,vol. 103,p. 274 - 282
[8]Russian Journal of Coordination Chemistry,2014,vol. 40,p. 634 - 642
[9]Chemical Communications,2015,vol. 51,p. 6512 - 6514
[10]Patent: JP2016/23165,2016,A .Location in patent: Paragraph 0051
[11]Patent: CN105399636,2016,A .Location in patent: Paragraph 0063
[12]Patent: JP2016/23164,2016,A .Location in patent: Paragraph 0044
[13]Patent: CN106946732,2017,A .Location in patent: Paragraph 0014; 0015
[14]Journal of Molecular Liquids,2019,vol. 294
[15]Journal of Coordination Chemistry,2019,vol. 72,p. 2295 - 2309

28
[ 381248-06-2 ]
[ 768-94-5 ]
3-(1-Adamantylamino)-5-(pyridin-2-yl)-1-phenyl-1,2-dihydropyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; In N-methyl-acetamide; water;	Example 176. 3-(1-Adamantylamino)-5-(2-pyridyl)-1-phenyl-1,2 dihydropyridin-2-one 27mg of <strong>[381248-06-2]3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one</strong> and 130mg of 1-adamantylamine were dissolved in 10ml of dimethylformamide. To the mixture was added 20mg of sodium hydride, followed by stirring at 130C in nitrogen atmosphere. After the reaction solution was cooled to room temperature, a saturated aqueous solution of ammonium chloride and water were added thereto, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 3mg of the title compound. 1H-NMR(400MHz, CDCl3); delta(ppm) 1.19-2.29(m,16H), 7.06-7.33(m,3H), 7.34-7.61(m,5H), 7.66-7.69(m,1H), 8.08-8.11(m,2H). ESI-Mass; 398 [M++H]

Reference： [1]Patent: EP1300396,2003,A1

29
[ 768-94-5 ]
[ 102-83-0 ]
[ 245421-04-9 ]
[ 1018478-88-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1308 - 1311

30
[ 768-94-5 ]
[ 56984-32-8 ]
[ 108-98-5 ]
[ 937743-04-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 3; [Show Image] The reaction of Compound 2 with phosphorus oxychloride gave Compound 6. The reaction of Compound 6 with thiophenol in the presence of cesium carbonate gave Compound A-2.

Reference： [1]Patent: EP1953145,2008,A1 .Location in patent: Page/Page column 21-22

31
[ 768-94-5 ]
[ 74-88-4 ]
[ 3717-38-2 ]

Reference： [1]Chemical Communications,2008,p. 2809 - 2811

32
[ 7343-33-1 ]
[ 768-94-5 ]
[ 1207947-26-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 839 - 848

33
[ 7560-50-1 ]
[ 768-94-5 ]
[ 1221411-79-5 ]

Yield	Reaction Conditions	Operation in experiment
88%		A mixture of methyl (2£)-3-(4-formylphenyl)acrylate (0.8 g, 4.2 mmol) and adamantan-1 -amine (1.3 g, 8.4 mmol) were stirred with MeOH (30 mL) for 3 h. To the reaction mixture was added NaBH4 (0.26 g, 6.7 mmol) and stirred for lOmin. The reaction mixture was diluted with water (300 mL). The precipitated white solid was filtered, washed with water (400 mL) and dried to give pure title compound (1.2 g, 88% yield).

Reference： [1]Patent: WO2010/43953,2010,A2 .Location in patent: Page/Page column 21

34
[ 2316-26-9 ]
[ 768-94-5 ]
C₂₃H₃₅NO₃ [ No CAS ]

Reference： [1]Journal of Combinatorial Chemistry,2010,vol. 12,p. 307 - 310

35
[ 4857-42-5 ]
[ 768-94-5 ]
[ 916922-08-2 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 1 (lg) in THF(30mL) was added n-Butyllithium(6.39mL, 2.71M hexane solution) at -78 °C under N2 atmosphere, then the reaction solution was allowed warm up to -30 °C. After cooling again to -78 °C, iodine(2.4g) in THF(20mL) was added to the reaction solution. After termination of this reaction, dilute hydrochloric acid was added to the solution. The solution was partitioned between water and EtOAc, extracted with EtOAc and washed with sodium thiosulfate soln., water and brine. The extraction was dried with MgSO4 and concentrated in vacuo. To a solution of the residue in DMF(25mL) were added 1-adamantanamine(1.43g), 1-hydroxybenzotriazole(1.28g) and 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride(1.81g), the resulting solution was stirred at room temp. After termination of this reaction, the mixture was partitioned between 2N HCl soln. and EtOAc, and extracted with EtOAc. The extraction was washed with 2N HCl soln., sat.NaHCO3 soln., brine successively then dried with MgSO4 and concentrated in vacuo. The residue was purified by silicagel columnchromatography to give 14 (2.47g).

Reference： [1]Patent: EP1894919,2008,A1 .Location in patent: Page/Page column 23

36
[ 768-94-5 ]
[ 274901-16-5 ]

Reference： [1]Patent: WO2011/101861,2011,A1
[2]Patent: WO2015/128718,2015,A1
[3]Patent: WO2015/128718,2015,A1
[4]Patent: WO2015/128718,2015,A1
[5]Patent: WO2015/128718,2015,A1
[6]Patent: WO2015/128718,2015,A1
[7]Patent: WO2015/128718,2015,A1

37
[ 23911-25-3 ]
[ 768-94-5 ]
C₃₀H₄₄N₄O₆^(2-)*2Na⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2011,vol. 69,p. 75 - 84

38
[ 101774-27-0 ]
[ 768-94-5 ]
[ 1378020-95-1 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5391 - 5402

39
[ 768-94-5 ]
[ 10406-06-1 ]
[ 1378020-94-0 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5391 - 5402

40
[ 768-94-5 ]
[ 130296-37-6 ]
[ 1386440-72-7 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 5965 - 5970

41
[ 768-94-5 ]
[ 1415409-74-3 ]
[ 156150-67-3 ]
[ 1415409-81-2 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 11504 - 11506,3

42
[ 612-57-7 ]
[ 768-94-5 ]
[ 1416219-24-3 ]

Reference： [1]Russian Journal of Organic Chemistry,2012,vol. 48,p. 1391 - 1406
Zh. Org. Khim.,2012,vol. 48,p. 1391 - 1406

43
[ 768-94-5 ]
[ 144072-30-0 ]
[ 1427505-24-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2804 - 2812

44
[ 768-94-5 ]
[ 144072-30-0 ]
[ 1427505-25-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2804 - 2812

45
[ 768-94-5 ]
[ 156866-52-3 ]
C₂₃H₃₄N₂O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2804 - 2812

46
[ 768-94-5 ]
[ 3685-22-1 ]
C₁₇H₂₇NO₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2804 - 2812

47
[ 16732-73-3 ]
[ 768-94-5 ]
[ 919726-42-4 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4093 - 4103

48
[ 16732-73-3 ]
[ 768-94-5 ]
[ 1432643-19-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4093 - 4103

49
[ 10242-10-1 ]
[ 768-94-5 ]
[ 1432642-66-4 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4093 - 4103

50
[ 768-94-5 ]
[ 4489-34-3 ]
[ 154118-02-2 ]
[ 1450821-98-3 ]

Reference： [1]Synthesis,2013,vol. 45,p. 1764 - 1784

51
[ 4744-50-7 ]
[ 768-94-5 ]
[ 405081-00-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4806 - 4809

52
[ 3163-76-6 ]
[ 768-94-5 ]
[ 1613153-14-2 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 2878 - 2882
Angew. Chem.,2014,p. 2922 - 2926,5

53
[ 768-94-5 ]
[ 34374-88-4 ]
[ 1613153-15-3 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 2878 - 2882
Angew. Chem.,2014,p. 2922 - 2926,5

54
[ 768-94-5 ]
[ 82732-07-8 ]
C₂₅H₃₆N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		(MM-2-113) Boc-HoPhe-OH (100 mg, 0.358 mmol), DEPBT (118 mg, 0.394 mmol, 1.10 equiv.) and Et3N (100 mu, , 0.716 mmol, 2.00 equiv) were dissolved at room temperature in anhydrous THF (2 mL) . After 15 minutes, 1-adamantylamine (60 mg, 0.394 mmol, 1.10 equiv) was added in one portion. After 12 hours, the mixture was diluted with EtOAc (15 mL) and washed with aqueous citric acid (10 mL, 10% w/v) and sat. NaHC03 (20 mL) . The organic phase was dried over Na2S04, filtered and concentrated. Flash chromatography (Si02, 20% EtOAc/hexanes ) gave 132 mg (89%) of the adamantyl amide. NMR (400 MHz, CDC13) delta 7.42 - 7.33 (m, 2H) , 7.28 (dt, J = 8.1, 3.8 Hz, 3H) , 5.71 (s, 1H) , 5.17 (d, J = 6.0 Hz, 1H) , 4.03 (m, 1H) , 2.86 - 2.64 (m, 2H) , 2.16 (t, J = 5.5 Hz, 3H) , 2.07 (t, J = 2.6 Hz, 6H) , 2.01 - 1.91 (m, 1H) , 1.80 - 1.70 (m, 6H) , 1.54 (d, J = 2.7 Hz, 9H) .

Reference： [1]Patent: WO2014/131023,2014,A1 .Location in patent: Page/Page column 161-162

55
[ 768-94-5 ]
[ 82732-07-8 ]
C₂₀H₂₈N₂O*ClH [ No CAS ]

Reference： [1]Patent: WO2014/131023,2014,A1

56
[ 1003-61-8 ]
[ 768-94-5 ]
C₁₄H₁₉N₃S [ No CAS ]