| Identification | More | [Name]
N-Benzyl-3-pyrrolidinol | [CAS]
775-15-5 | [Synonyms]
1-BENZYL-3-HYDROXYPYRROLIDINE
1-BENZYL-3-PYRROLIDINOL
1-BENZYLPYRROLIDINE-3-OL
N-BENZYL-3-PYRROLIDINOL
1-(benzyl)pyrrolidin-3-ol
1-N-BENZYL-3-HYDROXYPYRROLIDINE
1-BENZLY-3-HYDROXY PYRROLIDINE
1-Phenylmethylpyrrolidin-3-ol | [EINECS(EC#)]
212-273-5 | [Molecular Formula]
C11H15NO | [MDL Number]
MFCD00012132 | [Molecular Weight]
177.24 | [MOL File]
775-15-5.mol |
| Chemical Properties | Back Directory | [Boiling point ]
113-115 °C2 mm Hg(lit.)
| [density ]
1.07 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.548(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [form ]
clear liquid | [pka]
14.82±0.20(Predicted) | [color ]
Colorless to Light yellow to Light orange | [BRN ]
6039 | [InChI]
InChI=1S/C11H15NO/c13-11-6-7-12(9-11)8-10-4-2-1-3-5-10/h1-5,11,13H,6-9H2 | [InChIKey]
YQMXOIAIYXXXEE-UHFFFAOYSA-N | [SMILES]
N1(CC2=CC=CC=C2)CCC(O)C1 | [CAS DataBase Reference]
775-15-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi | [Risk Statements ]
R25:Toxic if swallowed.
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:Wear suitable protective clothing . | [RIDADR ]
UN 2810 6.1/PG 3
| [WGK Germany ]
1
| [F ]
10-34 | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Uses]
1-Benzyl-3-pyrrolidinol was used in preparation of:
- potent calcium antagonist, 1-benzyl-3-pyrrolidinyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
- (3R)-1-benzyl-3-methanesulfonyloxy pyrrolidine
| [Synthesis Reference(s)]
The Journal of Organic Chemistry, 51, p. 4296, 1986 DOI: 10.1021/jo00372a038 | [Synthesis]
The present embodiment is a method for the preparation of N-benzyl-3-hydroxypyrrolidine, which was carried out as follows: 250 g of 40 wt% aqueous benzylamine solution was added to a 500 mL four-necked flask and cooled to 10 °C. In an ice water bath, 102 g of 1,4-dichloro-2-butanol was added dropwise while stirring and the temperature was controlled at 15 °C. After the dropwise addition was completed in about 15 min, the system was transferred to a 500 mL autoclave, sealed, evacuated to a pressure of 1.0 ± 0.1 MPa, and simultaneously heated to 120 ± 2 °C, and the reaction was stirred for about 10 h. The disappearance of the raw material was monitored by GC. At the end of the reaction, cooled to room temperature, the material was discharged, 110g of sodium hydroxide was added in batches, and the temperature was controlled to be lower than 50°C in order to release the methylamine gas and precipitate a large amount of white solids, stirring for 1h. After filtration, the filtrate was stratified, and the upper organic phase was treated with 100mL of ethanol and 18g of anhydrous magnesium sulphate, stirring for 2-3h. It was filtered again, and the filtrate was concentrated under vacuum to get a yellow transparent oily liquid, and finally By vacuum distillation, 46.7 g of colorless and transparent N-benzyl-3-hydroxypyrrolidine was obtained with 64.8% yield and 99.3% purity (HPLC). | [References]
[1] Patent: CN106631956, 2017, A. Location in patent: Paragraph 0022; 0023; 0024; 0025; 0026; 0027 |
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