[ CAS No. 82572-04-1 ] {[proInfo.proName]}

Name: 82572-04-1|(R)-1-(Naphthalen-1-yl)ethanamine hydrochloride|98%
Brand: Ambeed
SKU: A196008
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Quality Control of [ 82572-04-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 82572-04-1 ]

SDS Specification

Alternatived Products of [ 82572-04-1 ]

Product Details of [ 82572-04-1 ]

CAS No. :	82572-04-1	MDL No. :	MFCD07369798
Formula :	C₁₂H₁₄ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZTNKTVBJMXQOBQ-SBSPUUFOSA-N
M.W :	207.70	Pubchem ID :	12314893
Synonyms :

Calculated chemistry of [ 82572-04-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	63.39
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) :	-5.03 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.57
Log Po/w (WLOGP) :	3.34
Log Po/w (MLOGP) :	3.12
Log Po/w (SILICOS-IT) :	2.77
Consensus Log Po/w :	2.56

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.84
Solubility :	0.0301 mg/ml ; 0.000145 mol/l
Class :	Soluble
Log S (Ali) :	-3.8
Solubility :	0.0328 mg/ml ; 0.000158 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.14
Solubility :	0.0149 mg/ml ; 0.0000718 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.26

Safety of [ 82572-04-1 ]

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 [ 82572-04-1 ]

* 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 [ 82572-04-1 ]
Downstream synthetic route of [ 82572-04-1 ]

[ 82572-04-1 ] Synthesis Path-Upstream 1~2

1
[ 585-50-2 ]
[ 82572-04-1 ]
[ 1005450-55-4 ]

Reference： [1] Tetrahedron Letters, 2008, vol. 49, # 1, p. 13 - 15

2
[ 82572-04-1 ]
[ 4657-12-9 ]
[ 163831-65-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: With sodium cyanoborohydride In methanol at 20℃; for 20 h; Stage #2: With hydrogenchloride In diethyl ether at 0℃; for 13 h;	General procedure: To a solution of amine hydrochloride (1 mmol) in methanol (10 mL) was added the aldehyde bisulfite adduct (1.12 mmol). To the resulting suspension NaCNBH₃ (2.5mmol) was slowly added, and the mixture was stirred for 20 h at rt. Then, the evaporation of the mixture furnished a residue which was partitioned between a 5N NaOH solution and EtOAc. The aqueous phase was extracted with EtOAc and thecombined organic phases were dried and evaporated to give a residue which was dissolved in Et₂O and treated with Et₂O-HCl (0.6 N). The resulting suspension was cooled for 13 h at 0°C and the precipitated white solid was filtered and dried in vacuo to afford the amine 12-24.

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 15, p. 2548 - 2550

[ 82572-04-1 ] Synthesis Path-Downstream 1~20

1
[ 82572-04-1 ]
(R)-1-(1-naphthyl)ethylammonium hexafluorophosphate [ No CAS ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 4319 - 4330

2
[ 585-50-2 ]
[ 82572-04-1 ]
[ 1005450-55-4 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 13 - 15

3
[ 50-00-0 ]
[ 82572-04-1 ]
[ 349-76-8 ]
[ 1224567-99-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; water; for 0.0833333h;Microwave irradiation;Product distribution / selectivity;	Method B; (R)-(I -naphthyl)ethylamine hydrochloride (III) (1.5 g), paraformaldehyde (0.3 g), 3-(trifluoromethyl)acetophenone (II) (1.8 g), 30% w/w aqueous hydrochloric acid (0.1 g), ethanol (4.5 g) and water (1.5 g) were charged into the reactor under stirring and reacted for 5 minutes under microwave irradiation (max 250W), until satisfactory conversion was observed via HPLC. Then water (10.0 g) and toluene (3.0 g) were added and the resulting suspension was stirred at 25C. The title compound (1.6 g) was isolated upon filtration at room temperature, washing with water and methyl 2- propanol and exsiccation at 500C.
	With hydrogenchloride; In ethanol; water; for 14h;Reflux;Product distribution / selectivity;	(R)-(I -naphthyl)ethylamine hydrochloride (III) (100.0 g), paraformaldehyde (15.9 g), 3-(trifluoromethyl)acetophenone (II) (135.7 g), 30% w/w aqueous hydrochloric acid(5.6 g), ethanol (150.0 g) and water (10.0 g) were charged into the reactor and stirred at reflux for 14 hrs, until satisfactory conversion was observed via HPLC. Then water (300.0 g) and toluene (305.0 g) were added and the mixture was stirred at 25C.The organic and aqueous layers were separated and additional water (200.0 g) was charged over the organic phase in order to favour the precipitation. The title compound (95.6 g) was isolated upon filtration at room temperature, washing with water and methyl tert-butyl ether and exsiccation at 500C.
	hydrogenchloride; In ethanol; water; for 0.0833333h;microwave irradiation;Product distribution / selectivity;	Method B(R)-(1-naphthyl)ethylamine hydrochloride (1.5 g), paraformaldehyde (0.3 g), 3- (trifiuoromethyl)acetophenone (1.8 g), 30% w/w aqueous hydrochloric acid (0.1 g), ethanol (4.5 g) and water (1.5 g) were charged into the reactor under stirring and reacted for 5 minutes under microwave irradiation (max 250W), until satisfactory conversion was observed via HPLC. Then water (10.0 g) and toluene (3.0 g) were added and the resulting suspension was stirred at 25C. The title compound (1.6 g) was isolated upon filtration at room temperature, washing with water and methyl 2- propanol and exsiccation at 50C.

Reference： [1]Patent: WO2010/49293,2010,A2 .Location in patent: Page/Page column 26
[2]Patent: WO2010/94674,2010,A2 .Location in patent: Page/Page column 18
[3]Patent: WO2011/29833,2011,A1 .Location in patent: Page/Page column 16-17

4
[ 941-98-0 ]
[ 82572-04-1 ]

Reference： [1]Synthetic Communications,2011,vol. 41,p. 341 - 346

5
[ 1073144-62-3 ]
[ 82572-04-1 ]

Reference： [1]Synthetic Communications,2011,vol. 41,p. 341 - 346

6
[ 1956-40-7 ]
[ 82572-04-1 ]

Reference： [1]Synthetic Communications,2011,vol. 41,p. 341 - 346

7
[ 82572-04-1 ]
[ 364782-34-3 ]

Reference： [1]Patent: WO2011/29833,2011,A1
[2]Patent: WO2011/29833,2011,A1

8
[ 82572-04-1 ]
[ 1224568-02-8 ]

Reference： [1]Patent: WO2011/29833,2011,A1

9
[ 82572-04-1 ]
[ 1273259-50-9 ]

Reference： [1]Patent: WO2011/29833,2011,A1

10
[ 82572-04-1 ]
[ 1273259-52-1 ]

Reference： [1]Patent: WO2011/29833,2011,A1
[2]Patent: WO2011/29833,2011,A1

11
C₅₂H₆₆O₇ [ No CAS ]
[ 82572-04-1 ]
C₁₂H₁₃N*C₅₂H₆₆O₇*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; chloroform; at 25℃;Thermodynamic data;	General procedure: The ability of crown ethers to coordinate to amines and amino acid methyl ester hydrochloride salts was investigated using UV spectroscopic titration. The UV-vis spectra were measured at 25 +/- 0.1 C with a thermostated cell compartment by a CARY 100 spectrophotometer. The same concentration of guest solution was added to the sample cell and reference cell. The maximum wavelengths are 327 nm for 6-7 to NEA-HCl and 281 nm for other host-guest systems. CHCl3/MeOH (2:1) was used as the solvent. The concentration of the hosts is 5.0 × 10-5 mol dm-3 with the increasing concentration of the added guest.

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 381 - 386

12
C₅₂H₆₆O₇ [ No CAS ]
[ 82572-04-1 ]
C₁₂H₁₃N*C₅₂H₆₆O₇*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; chloroform; at 25℃;Thermodynamic data;	General procedure: The ability of crown ethers to coordinate to amines and amino acid methyl ester hydrochloride salts was investigated using UV spectroscopic titration. The UV-vis spectra were measured at 25 +/- 0.1 C with a thermostated cell compartment by a CARY 100 spectrophotometer. The same concentration of guest solution was added to the sample cell and reference cell. The maximum wavelengths are 327 nm for 6-7 to NEA-HCl and 281 nm for other host-guest systems. CHCl3/MeOH (2:1) was used as the solvent. The concentration of the hosts is 5.0 × 10-5 mol dm-3 with the increasing concentration of the added guest.

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 381 - 386

13
[ 21172-41-8 ]
[ 82572-04-1 ]
[ 226256-56-0 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium tris(acetoxy)borohydride; at 20℃; for 2h;	Example 3: Synthesis of compound (I): Cinacalcet hydrochloride A solution of compound (II) (1.0 g, 4.95 mmol) and (R)-1-(1-naphthyl)ethylamine hydrochloride (III) (1.03 g, 4.95 mmol) in methanol (10 ml), kept under stirring at 20C, is treated with solid NaBH(OAc)3 (2.10 g, 9.89 mmol) in portions. After 2 hours the suspended solid is filtered and the solution is concentrated under reduced pressure. The residue is taken up into toluene and washed first with 1% HCl, then with 5% NaOH. The phases are separated and the organic one is concentrated under reduced pressure to afford a residue substantially consisting of Cinacalcet base. 1H NMR (300 MHz, CDCl3), ppm: 8.20 (d, 1H, J 7.5 Hz), 7.88 (m, 1H), 7.76 (d, 1H, J 8.1 Hz), 7.66 (d, 1H, J 7.2 Hz), 7.55-7.43 (m, 5H), 7.38-7.30 (m, 2H), 4.63 (q, 1H, J 6.6 Hz), 2.80-2.56 (m, 4H), 1,84 (m, 2H), 1.50 (d, 2H, J 6.6 Hz).

Reference： [1]Patent: EP2327684,2011,A1 .Location in patent: Page/Page column 6-7

14
[ 82572-04-1 ]
[ 4657-12-9 ]
[ 163831-65-0 ]

Yield	Reaction Conditions	Operation in experiment
67%		General procedure: To a solution of amine hydrochloride (1 mmol) in methanol (10 mL) was added the aldehyde bisulfite adduct (1.12 mmol). To the resulting suspension NaCNBH3 (2.5mmol) was slowly added, and the mixture was stirred for 20 h at rt. Then, the evaporation of the mixture furnished a residue which was partitioned between a 5N NaOH solution and EtOAc. The aqueous phase was extracted with EtOAc and thecombined organic phases were dried and evaporated to give a residue which was dissolved in Et2O and treated with Et2O-HCl (0.6 N). The resulting suspension was cooled for 13 h at 0C and the precipitated white solid was filtered and dried in vacuo to afford the amine 12-24.