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164148-92-9

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164148-92-9 Structure

164148-92-9 Structure
IdentificationMore
[Name]

6-AMINO-2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
[CAS]

164148-92-9
[Synonyms]

6-AMINO-2-BOC-3,4-DIHYDRO-1H-ISOQUINOLINE
6-AMINO-2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
6-AMINO-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER
TERT-BUTYL 6-AMINO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE
[Molecular Formula]

C14H20N2O2
[MDL Number]

MFCD03426351
[Molecular Weight]

248.32
[MOL File]

164148-92-9.mol
Chemical PropertiesBack Directory
[Boiling point ]

394.7±42.0 °C(Predicted)
[density ]

1.145±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C(protect from light)
[pka]

4.35±0.20(Predicted)
[Appearance]

Off-white to yellow Solid
[InChI]

InChI=1S/C14H20N2O2/c1-14(2,3)18-13(17)16-7-6-10-8-12(15)5-4-11(10)9-16/h4-5,8H,6-7,9,15H2,1-3H3
[InChIKey]

OLOIFCYZWOTWRO-UHFFFAOYSA-N
[SMILES]

C1C2=C(C=C(N)C=C2)CCN1C(OC(C)(C)C)=O
[CAS DataBase Reference]

164148-92-9(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H332-H335
[Precautionary statements ]

P261-P280-P305+P351+P338
[Hazard Codes ]

Xn,N
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
[RIDADR ]

UN2811
[HS Code ]

2922390090
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium hydroxide-->Ethyl acetate-->Sulfuric acid-->Dichloromethane-->Acetic acid-->Potassium carbonate-->Triethylamine-->Ammonia-->Sodium bicarbonate-->Palladium-->1,4-Dioxane-->Sodium borohydride-->Isopropyl alcohol-->Di-tert-butyl dicarbonate-->polyphosphoric acid-->Trifluoroacetic anhydride-->Ethyl formate-->Paraformaldehyde-->Ammonium acetate-->Potassium nitrate-->1,2,3,4-Tetrahydroisoquinoline-->2-(4-Bromophenyl)ethylamine
Hazard InformationBack Directory
[Uses]

6-Amino-2-N-Boc-1,2,3,4-tetrahydroisoquinoline is used as a reagent in the preparation of potent and long acting oral factor Xa inhibitors.
[Synthesis]

2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-6-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester

1154424-63-1

6-AMINO-2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE

164148-92-9

General procedure for the synthesis of 6-amino-2-N-BOC-1,2,3,4-tetrahydro-isoquinoline from compound (CAS:1154424-63-1): ammonium formate (3.68 g, 57.5 mmol) was added to a stirred ethanol (EtOH, 25 mL) solution of compound 2 (2.2 g, 5.75 mmol) and the reaction mixture was heated to refluxed for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature and filtered through a diatomaceous earth bed to remove insoluble impurities. Subsequently, the diatomaceous earth bed and the filtrate were combined and concentrated under reduced pressure to afford compound 3 (1.3 g, 91% yield) as a dark brown oil, which could be used in subsequent reactions without further purification.

[References]

[1] Patent: WO2009/158571, 2009, A1. Location in patent: Page/Page column 165; 167; 168
Spectrum DetailBack Directory
[Spectrum Detail]

6-AMINO-2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(164148-92-9)1HNMR
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